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Results: 681 Rentals

  • Spacious 3BR 3BA Pet Friendly Resort Condo
    From $838 per night (USD)

    VRBO

    Spacious 3BR 3BA Pet Friendly Resort Condo

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Escape to our spacious 3-bed, 3-bath mountain condo, perfect for families or groups. Enjoy cozy evenings by the gas fire ...

    From $838 per night (USD)

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  • Ledges 78 with Wintergreen Advantage
    From $507 per night (USD)

    Expedia

    Ledges 78 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Ledges Valley View Retreat Take in beautiful valley views from this top-floor, end-unit condo in Ledges at Wintergreen ...

    From $507 per night (USD)

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  • Tanners Ridge 21 with Wintergreen Advantage
    From $465 per night (USD)

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    Tanners Ridge 21 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Tanners Ridge Mountain Escape Enjoy a relaxing retreat in this 2-bedroom, 2-bath condo in Tanners Ridge, located in Win ...

    From $465 per night (USD)

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  • Overlook 29 with Wintergreen Advantage
    From $507 per night (USD)

    Expedia

    Overlook 29 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Overlook Scenic Mountain Retreat Take in the beauty of Wintergreen from this 2-bedroom, 2-bath condo in the Overlook co ...

    From $507 per night (USD)

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  • Ledges 72  with Wintergreen Advantage
    From $667 per night (USD)

    VRBO

    Ledges 72 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Ledges Spacious Mountain Escape Enjoy a relaxing Wintergreen getaway in this spacious 3-bedroom, 3-bath condo at Ledges ...

    From $667 per night (USD)

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  • Ledges 52  with Wintergreen Advantage
    From $667 per night (USD)

    Expedia

    Ledges 52 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Ledges Peaceful Mountain Retreat Escape to a peaceful mountain getaway in this spacious 3-bedroom, 3-bath condo at Ledg ...

    From $667 per night (USD)

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  • Laurelwood 48 with Wintergreen Advantage
    From $465 per night (USD)

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    Laurelwood 48 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Laurelwood Mountain Escape Escape to the mountains in this inviting 2-bedroom, 2-bath retreat in Laurelwood at Wintergr ...

    From $465 per night (USD)

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  • Northridge 06  with Wintergreen Advantage
    From $604 per night (USD)

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    Northridge 06 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Northridge Tranquil Mountain Retreat Escape to the tranquility of Wintergreen Resort in this spacious 3-bedroom, 3-bath ...

    From $604 per night (USD)

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  • Stoneridge 81 with Wintergreen Advantage
    From $604 per night (USD)

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    Stoneridge 81 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Stoneridge Cozy Mountain Escape Enjoy a relaxing mountain getaway in this spacious 3-bedroom, 3-bath condo at Stoneridg ...

    From $604 per night (USD)

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  • Stoneridge 70  with Wintergreen Advantage
    From $604 per night (USD)

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    Stoneridge 70 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Stoneridge Spacious Mountain Retreat Settle into a spacious mountain getaway in this 3-bedroom, 3-bath condo at Stoneri ...

    From $604 per night (USD)

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  • Fully Loaded 8BR in Wintergreen! Sleeps 23
    From $1028 per night (USD)

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    Fully Loaded 8BR in Wintergreen! Sleeps 23

    Bedrooms:
    4
    Bathrooms:
    8
    Sleeps:
    23

    Welcome to Crawfords Escape, a designer-decorated 8BR 4500 sf chalet in scenic Wintergreen that sleeps 23. Outside, enjo ...

    From $1028 per night (USD)

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  • Newly Remodeled 4BR/4.5BA Golf Front Townhome. Pet Friendly!
    From $526 per night (USD)

    Expedia

    Newly Remodeled 4BR/4.5BA Golf Front Townhome. Pet Friendly!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    9

    Completely Remodeled Golf Front Townhome | Walk to Ski Shuttle Stop, Spa & Fitness Center | Pet-Friendly Experience the ...

    From $526 per night (USD)

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  • Escape to Wintergreen Resort! Our pet & kid-friendly 2BR/2BA townhome is steps from skiing, dining & the Market. Hike, ski, swim, or sip at nearby wineries & breweries—adventure awaits year-round!
    From $506 per night (USD)

    VRBO

    Escape to Wintergreen Resort! Our pet & kid-friendly 2BR/2BA townhome is steps from skiing, dining & the Market. Hike, ski, swim, or sip at nearby wineries & breweries—adventure awaits year-round!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wintergreen Resort is a fantastic, all season destination, with adventures for everyone! We are a pet and kid friendly, ...

    From $506 per night (USD)

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  • Family-favorite rental nestled in the woods at the top of the Wintergreen Resort
    From $405 per night (USD)

    VRBO

    Family-favorite rental nestled in the woods at the top of the Wintergreen Resort

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    The Blue Ridge Mountains are calling you to this 3-level, 4 bed/3 bath home for an epic getaway! A family-favorite renta ...

    From $405 per night (USD)

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  • The Honey Den - Your Family's Summer Retreat - Outdoor Pools, Nature, Adventure
    From $472 per night (USD)

    VRBO

    The Honey Den - Your Family's Summer Retreat - Outdoor Pools, Nature, Adventure

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    11

    Welcome to The Honey Den - a warm 5BR, 4.5BA mountain home designed for slow mornings, golden-hour decks, and easy toget ...

    From $472 per night (USD)

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  • Little Haven Cottage: Walk to Meade Tasting
    From $467 per night (USD)

    Expedia

    Little Haven Cottage: Walk to Meade Tasting

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Escape to the serenity of the Blue Ridge Mountains with a stay at our cozy, well-appointed cottage located directly on t ...

    From $467 per night (USD)

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  • Serenity Cabin-Woodland Retreat
    From $462 per night (USD)

    VRBO

    Serenity Cabin-Woodland Retreat

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Serenity Cabin: Your Perfect Woodland Retreat Nestled among the trees, this recently renovated timber-framed ...

    From $462 per night (USD)

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  • Amazing Mountain Views, Hot Tub and Close to Wineries and Breweries
    From $505 per night (USD)

    Expedia

    Amazing Mountain Views, Hot Tub and Close to Wineries and Breweries

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Sit back, relax, and soak in the views. The Rockfish Retreat is nestled in the foothills of the Blue Ridge Mountains, ri ...

    From $505 per night (USD)

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    Details
  • Wren Time, Wintergreen Mountain Retreat with Hot Tub
    From $536 per night (USD)

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    Wren Time, Wintergreen Mountain Retreat with Hot Tub

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    A Mountain home nestled in the Blue Ridge Mountains with breathtaking valley views and mesmerizing sunrises! The propert ...

    From $536 per night (USD)

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  • Authentic Log Cabin-
    From $488 per night (USD)

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    Authentic Log Cabin-

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Come enjoy our beautifully decorated authentic log cabin which provides the perfect setting for your weekend get-a-way o ...

    From $488 per night (USD)

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  • Endless Mountain Top Views from All The Way Up!
    From $330 per night (USD)

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    Endless Mountain Top Views from All The Way Up!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Our warm and inviting condo combines amazing proximity to the ski slopes with to-die-for views of the Blue Ridge Mountai ...

    From $330 per night (USD)

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  • Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
    From $241 per night (USD)

    Expedia

    Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Rosie's Retreat (FKA: Ro's Retreat) Come enjoy this cozy 3 bedroom/3 bath condo located on the 18th hole of Devils Knob. ...

    From $241 per night (USD)

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  • Modern Wintergreen Cabin with Hot Tub, Sauna
    From $398 per night (USD)

    VRBO

    Modern Wintergreen Cabin with Hot Tub, Sauna

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    Welcome to Blue Ridge Hollow! This designer-decorated cabin in the heart of Wintergreen has one of the best outdoor spac ...

    From $398 per night (USD)

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  • Coin Cottage farmhouse on 151 Trail in Nelson County
    From $393 per night (USD)

    Expedia

    Coin Cottage farmhouse on 151 Trail in Nelson County

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This 1946 farmhouse has been remodeled this recently. Talk about location!!! This home is located within 1 mile of Silve ...

    From $393 per night (USD)

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  • Leaf-Peeping at Oak Ledge! Trails+Tastings+Peace
    From $387 per night (USD)

    VRBO

    Leaf-Peeping at Oak Ledge! Trails+Tastings+Peace

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    <p>You'll find ski privileges, a kayak, and more on site at this family-friendly cabin. There's convenient onsite parkin ...

    From $387 per night (USD)

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  • 4BD Modern Cabin | Patio, Game Loft, Golf Course View
    From $645 per night (USD)

    Expedia

    4BD Modern Cabin | Patio, Game Loft, Golf Course View

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to the Castor Cabin - an impeccably decorated home in the heart of Wintergreen! This recently renovated space an ...

    From $645 per night (USD)

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  • Insane Mountain Views - New Listing
    From $1506 per night (USD)

    VRBO

    Insane Mountain Views - New Listing

    Bedrooms:
    9
    Bathrooms:
    7
    Sleeps:
    18

    One of the largest homes in Wintergreen with 7 bedrooms and 10 bathrooms. The floor-to-ceiling windows offer a sunrise ...

    From $1506 per night (USD)

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  • Pet Friendly Cozy Mountain Retreat-sleeps 10!
    From $472 per night (USD)

    Expedia

    Pet Friendly Cozy Mountain Retreat-sleeps 10!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    A quiet and relaxing escape for up to 10 people only a 2 minute drive to the Wintergreen Village. Parking for up to 3 ve ...

    From $472 per night (USD)

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    Details
  • Stunning Views, Hot Tub, Impeccable Design
    From $715 per night (USD)

    VRBO

    Stunning Views, Hot Tub, Impeccable Design

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Ryder's Ridge, a designer-decorated home on a quiet street in Wintergreen with amazing mountain views! Watch ...

    From $715 per night (USD)

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  • Ski-In/Ski-Out Comfy Condo
    From $174 per night (USD)

    Expedia

    Ski-In/Ski-Out Comfy Condo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Great condo for a couple or for a small family. Condo is a ski-in/ski-out on the ground floor-no stairs to tackle! Enter ...

    From $174 per night (USD)

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  • Luxury mountain home Ski- in-Ski out
    From $1084 per night (USD)

    VRBO

    Luxury mountain home Ski- in-Ski out

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    9

    Gorgeous Blue Ridge Mountain Weekend Escape! Well mannered Pets welcomed with owners permission. Must ask ahead. We welc ...

    From $1084 per night (USD)

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  • Slope Side Suite
    From $180 per night (USD)

    Expedia

    Slope Side Suite

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    Escape to the mountains and cozy up at this incredibly central cabin at Wintergreen Resort (a short walk to ski slopes). ...

    From $180 per night (USD)

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  • Blue Ridge Cabin · 3 Levels · 3 Scenic Decks · Music Game Room · Hot Tub· Arcade
    From $664 per night (USD)

    VRBO

    Blue Ridge Cabin · 3 Levels · 3 Scenic Decks · Music Game Room · Hot Tub· Arcade

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to the Rockstar Ridge, a 3,300 sq. ft. cabin retreat perched atop a ridge near Wintergreen Resort in Virginia's ...

    From $664 per night (USD)

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  • Wintergreen 1bed Condo, Walk to slopes, close to Hiking, Breweries, Wineries
    From $195 per night (USD)

    Expedia

    Wintergreen 1bed Condo, Walk to slopes, close to Hiking, Breweries, Wineries

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Walking distance to the slopes 🎿🗻 located in Wintergreen New 1BR 1BA centrally located in Wintergreen Enjoy the beau ...

    From $195 per night (USD)

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  • Wintergreen Resort Retreat w/ Skiing Access!
    From $373 per night (USD)

    VRBO

    Wintergreen Resort Retreat w/ Skiing Access!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Kick back and relax at this charming 3-bedroom, 3-bath Wintergreen Resort condo! Tucked away in the Blue Ridge Mountains ...

    From $373 per night (USD)

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  • Snug Wintergreen Resort Studio: Ski In & Out!
    From $192 per night (USD)

    Expedia

    Snug Wintergreen Resort Studio: Ski In & Out!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    The ultimate Blue Ridge Mountain adventure awaits with this lovely cabin-inspired studio as your home base! Nestled in W ...

    From $192 per night (USD)

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  • Embrace the mountain lifestyle in this delightful true ski-in/ski-out condo in Wintergreen!
    From $361 per night (USD)

    VRBO

    Embrace the mountain lifestyle in this delightful true ski-in/ski-out condo in Wintergreen!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    5

    Escape to the beauty of Wintergreen Resort in every season! Our cozy 1-bedroom, 2-bath condo is just steps from the slop ...

    From $361 per night (USD)

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  • Spacious + Serene Mtn Top Escape, 4 En Suites
    From $381 per night (USD)

    Expedia

    Spacious + Serene Mtn Top Escape, 4 En Suites

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to our mountain top home, just minutes from the heart of the resort, connected to walking trails, and with spect ...

    From $381 per night (USD)

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  • Welcome to our stunning 3-bedroom, 2-bathroom house nestled in the heart of Wintergreen, Virginia.
    From $674 per night (USD)

    VRBO

    Welcome to our stunning 3-bedroom, 2-bathroom house nestled in the heart of Wintergreen, Virginia.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to this enchanting 3-bedroom, 2-bathroom home located in the picturesque Wintergreen, VA. This delightful mounta ...

    From $674 per night (USD)

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  • Roudy’s Retreat: Secluded Mountain Cabin with Hot Tub and Private Pond
    From $641 per night (USD)

    Expedia

    Roudy’s Retreat: Secluded Mountain Cabin with Hot Tub and Private Pond

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    10

    Escape to this spacious retreat with a hot tub and everything you need to get away. The wooden interior will take you to ...

    From $641 per night (USD)

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    Details
  • Pet-Friendly Snowflake Inn: Cozy Retreat with Sauna, Jacuzzi & Family Fun!
    From $1272 per night (USD)

    VRBO

    Pet-Friendly Snowflake Inn: Cozy Retreat with Sauna, Jacuzzi & Family Fun!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    The Snowflake Inn is a family friendly home located in the coveted Blackrock district in the heart of the Wintergreen Re ...

    From $1272 per night (USD)

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  • Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
    From $323 per night (USD)

    Expedia

    Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Spy Run Hideaway is truly a one-of-a-kind experience that is quiet and secluded on 17 acres that is nestled in the Blue ...

    From $323 per night (USD)

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  • Hickory Hideaway- 5 BR 4 BA with game room and indoor fire place
    From $560 per night (USD)

    VRBO

    Hickory Hideaway- 5 BR 4 BA with game room and indoor fire place

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to the Hickory Hideaway! This 5 BR, 4 BA home is located in the heart of Wintergreen Resort. The home features ...

    From $560 per night (USD)

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    Details
  • 3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes
    From $448 per night (USD)

    Expedia

    3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to 3 Ridges Vista. Stunning views of the Blue Ridge Mountains including the famous Three Ridges peaks. This full ...

    From $448 per night (USD)

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    Details
  • Luxe Wintergreen Resort Escape w/ Hot Tub!
    From $720 per night (USD)

    VRBO

    Luxe Wintergreen Resort Escape w/ Hot Tub!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Treat your family to a mountainside retreat and book this 4-bedroom, 3-bath Roseland vacation rental! This amenity-packe ...

    From $720 per night (USD)

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    Details
  • Bright & Modern 5 BR Wintergreen Home; Minutes from Hiking, Skiing, and Wineries
    From $573 per night (USD)

    Expedia

    Bright & Modern 5 BR Wintergreen Home; Minutes from Hiking, Skiing, and Wineries

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    11

    Welcome to Hiker’s Haven! Located in Wintergreen Resort, Hiker’s Haven is the perfect retreat for all seasons. After a ...

    From $573 per night (USD)

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    Details
  • Idyllic Wintergreen Condo w/ Resort Amenities
    From $203 per night (USD)

    VRBO

    Idyllic Wintergreen Condo w/ Resort Amenities

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    With easy access to resort amenities and the great outdoors, this Wintergreen Resort vacation rental is the perfect spot ...

    From $203 per night (USD)

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  • Private One Bedroom by Mountain Stream
    From $291 per night (USD)

    VRBO

    Private One Bedroom by Mountain Stream

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Cabin Barnwood is a very private one bedroom, with a nice patio and creek. The bedroom has a queen pencil poster bed, a ...

    From $291 per night (USD)

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  • Logwood Cabin Pre Civil War
    From $278 per night (USD)

    VRBO

    Logwood Cabin Pre Civil War

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Pre-Civil War Log cabin Cabin Creekwood is a family-owned business providing relaxing getaways in the Blue Ridge Mounta ...

    From $278 per night (USD)

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  • Pet Friendly Three Bedroom in Blue Ridge Mountains
    From $373 per night (USD)

    VRBO

    Pet Friendly Three Bedroom in Blue Ridge Mountains

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Oakwood is a large three bedroom, two bath cabin, all on one level. The master bedroom contains a queen bed, plus a s ...

    From $373 per night (USD)

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  • Pet Friendly Two Bedroom in Blue Ridge Mtns
    From $292 per night (USD)

    VRBO

    Pet Friendly Two Bedroom in Blue Ridge Mtns

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    A very comfortable two bedroom, Mountainwood gives plenty of room to spread out. The main room is nice and open, includ ...

    From $292 per night (USD)

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  • Cozy Modern Cabin near Wintergreen and Bold Rock
    From $424 per night (USD)

    Expedia

    Cozy Modern Cabin near Wintergreen and Bold Rock

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy your stay away from town with this cozy modern cabin located in the foothills of Wintergreen. The home is equipped ...

    From $424 per night (USD)

    Expedia

    Details
  • 6 BR home, NEW HOT TUB, EV Charger.Walk to slopes! Close to wineries & breweries
    From $756 per night (USD)

    VRBO

    6 BR home, NEW HOT TUB, EV Charger.Walk to slopes! Close to wineries & breweries

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    *NEW HOT TUB* 5/6 BR spacious home for friends and family retreat with EV Charger Level 2! We offer a 10% discount on th ...

    From $756 per night (USD)

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    Details
  • Adventure Awaits
    From $410 per night (USD)

    Expedia

    Adventure Awaits

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    13

    Summary: Welcome to Adventure Awaits at Wintergreen Resort, your ultimate destination for year-round excitement nestled ...

    From $410 per night (USD)

    Expedia

    Details
  • Wintergreen Resort Vacation Rental w/ Balcony!
    From $216 per night (USD)

    VRBO

    Wintergreen Resort Vacation Rental w/ Balcony!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the beauty of Wintergreen Resort, VA, and indulge in a memorable stay at this 2-bedroom, 2-bathroom vacation re ...

    From $216 per night (USD)

    VRBO

    Details
  • Wintergreen Resort Vacation Rental w/ Pool Access!
    From $302 per night (USD)

    Expedia

    Wintergreen Resort Vacation Rental w/ Pool Access!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    No matter the season, you’ll have easy access to endless outdoor adventures when you stay at this cozy Wintergreen Resor ...

    From $302 per night (USD)

    Expedia

    Details
  • Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
    From $213 per night (USD)

    VRBO

    Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Pet-Friendly One Bedroom Condo on a Scenic Golf Course Indulge in relaxation at this tranquil Wintergreen haven. No mat ...

    From $213 per night (USD)

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  • Serene Wintergreen Retreat, Nestled in the Trees
    From $419 per night (USD)

    Expedia

    Serene Wintergreen Retreat, Nestled in the Trees

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to our cozy Wintergreen cabin in the trees! You'll truly feel at peace with nature on the three levels of decks ...

    From $419 per night (USD)

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  • Afton escape centrally located on the brew trail
    From $205 per night (USD)

    VRBO

    Afton escape centrally located on the brew trail

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Centrally located on the brew trail, this home is a short drive to the local wineries, breweries and distilleries, as we ...

    From $205 per night (USD)

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  • Welcome to Winterhaven!  5BR/4BA .5mi from lodge!
    From $502 per night (USD)

    Expedia

    Welcome to Winterhaven! 5BR/4BA .5mi from lodge!

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to Winterhaven! Recent rental with new furniture, TVS, and updates throughout and flat paved driveway. Locat ...

    From $502 per night (USD)

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  • Coastal Farmhouse Getaway!
    From $503 per night (USD)

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    Coastal Farmhouse Getaway!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Take it easy at this unique and tranquil getaway. This fully renovated historic farmhouse sits on 4 acres on Windmill Po ...

    From $503 per night (USD)

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  •  Your Mountain Cabin Getaway Awaits!
    From $490 per night (USD)

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    Your Mountain Cabin Getaway Awaits!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    EVERYTHING YOU NEED! Exquisitely furnished and decorated private cabin retreat in the mountain woods just minutes from t ...

    From $490 per night (USD)

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  • Whispering Pines with Wintergreen Advantage
    From $504 per night (USD)

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    Whispering Pines with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy the fresh mountain air and picturesque forested surroundings when you stay at Whispering Pines, a secluded 3-bedro ...

    From $504 per night (USD)

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  • Orchard House with Wintergreen Advantage
    From $746 per night (USD)

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    Orchard House with Wintergreen Advantage

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    A Beautifully Appointed Mountain Retreat at Wintergreen Orchard House is a distinctive five-bedroom, six-and-a-half-bath ...

    From $746 per night (USD)

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  • Black Dog Treehouse with Wintergreen Advantage
    From $504 per night (USD)

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    Black Dog Treehouse with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Do you hear that? The mountains are calling, and this is your perfect home away from home. The Black Dog Treehouse is a ...

    From $504 per night (USD)

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  • Luxury Designer Home, Dome and Top amenities
    From $792 per night (USD)

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    Luxury Designer Home, Dome and Top amenities

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    16

    Welcome to Wintergreen - Mountain View Retreat! Discover the latest listing in Wintergreen – a spacious mountain retreat ...

    From $792 per night (USD)

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  • Hot Tub Pool Pac Man Foosball Dogs OK Tennis Golf
    From $385 per night (USD)

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    Hot Tub Pool Pac Man Foosball Dogs OK Tennis Golf

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    4min to ski, walk to trails! Endless activities: apple picking, breweries/wineries, hiking, lake, horseback, golf, tenni ...

    From $385 per night (USD)

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  • Hot Tub Sauna EV Charger Golden Tee Pool Tennis
    From $460 per night (USD)

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    Hot Tub Sauna EV Charger Golden Tee Pool Tennis

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    14

    5min to ski slopes! New hot tub and EV charger. Perfect for 2-3 families. After day of adventures, gather for sunset on ...

    From $460 per night (USD)

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  • Sip 'n Dip: Hot Tub Foosball Pool Table Ping Pong
    From $404 per night (USD)

    VRBO

    Sip 'n Dip: Hot Tub Foosball Pool Table Ping Pong

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Easy access to Wintergreen Resort, hiking trails, tennis, golf, and breweries/wineries. Great for families and groups. ...

    From $404 per night (USD)

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  • Cozy House at Wintergreen with hot tub/firepit/fireplace & all amenities included and pool access!
    From $676 per night (USD)

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    Cozy House at Wintergreen with hot tub/firepit/fireplace & all amenities included and pool access!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to our cozy 4-bedroom, 3.5-bathroom home in Wintergreen Resort, VA. Enjoy a spacious living room with a fireplac ...

    From $676 per night (USD)

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  • Mountain House Overlooking Rockfish Valley
    From $505 per night (USD)

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    Mountain House Overlooking Rockfish Valley

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unique octagonal house offering incredible views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 ...

    From $505 per night (USD)

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  • Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly
    From $634 per night (USD)

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    Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    16

    Welcome to "Above the Clouds", your year-round retreat in the heart of Wintergreen. Our spacious house, nestled just min ...

    From $634 per night (USD)

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  • Twin Ponds: King Beds, Hot tub, Gameroom, 75\ TV, Foosball, Air Hockey, PingPong
    From $374 per night (USD)

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    Twin Ponds: King Beds, Hot tub, Gameroom, 75\" TV, Foosball, Air Hockey, PingPong

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    About this space Welcome to Twin Ponds, a beautifully appointed & fun-filled mountain house in Wintergreen Resort's Ston ...

    From $374 per night (USD)

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  • Cozy Cabin in the Wintergreen Retreat Collection of Fine Homes
    From $334 per night (USD)

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    Cozy Cabin in the Wintergreen Retreat Collection of Fine Homes

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Escape to bespoke, rustic luxury in the heart of Wintergreen Resort! Come enjoy our beautifully decorated, authentic l ...

    From $334 per night (USD)

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  • Escape the Heat • 10° Cooler Mtn Oasis • Hot Tub • Fire Pit • 4 Ensuite BRs
    From $627 per night (USD)

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    Escape the Heat • 10° Cooler Mtn Oasis • Hot Tub • Fire Pit • 4 Ensuite BRs

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    PROPERTY OVERVIEW: Escape the summer heat at 3,800 feet in the Blue Ridge Mountains! Often up to 10° cooler than the va ...

    From $627 per night (USD)

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  • Wintergreen Ski Resort Condo w/ Golf Access!
    From $238 per night (USD)

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    Wintergreen Ski Resort Condo w/ Golf Access!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Days spent shredding the slopes and cozy nights by the fireplace await when you stay at this charming 2-bedroom, 2-bathr ...

    From $238 per night (USD)

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    Details
  • Wintergreen Resort Getaway w/ Deck, Mountain View!
    From $355 per night (USD)

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    Wintergreen Resort Getaway w/ Deck, Mountain View!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    13

    Enjoy easy access to all of the excitement Wintergreen Resort has to offer at this charming Roseland vacation rental! Lo ...

    From $355 per night (USD)

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  • The Brew Ridge Trail's Most Unique Home.  Sleeps 12
    From $646 per night (USD)

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    The Brew Ridge Trail's Most Unique Home. Sleeps 12

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Surely you've heard about the "Almost World-Famous Boogie Nights Manor". The Boog has remained the #1 rated STR property ...

    From $646 per night (USD)

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  • Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!
    From $214 per night (USD)

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    Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Just 3-5 minutes walk to the Slopes, Ski Check in, the Market, Restaurants, Shops and Entertainment, our newly renovated ...

    From $214 per night (USD)

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  • Heaven On Earth ~ Wintergreen Mountain
    From $1378 per night (USD)

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    Heaven On Earth ~ Wintergreen Mountain

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    16

    Nestled amid the pristine beauty of the towering mountains, Heaven On Earth provides the perfect alpine escape for those ...

    From $1378 per night (USD)

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  • Wintergreen Oasis - PRIVATE POOL & SAUNA
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    Wintergreen Oasis - PRIVATE POOL & SAUNA

    Bedrooms:
    4
    Bathrooms:
    7
    Sleeps:
    16

    This Wintergreen Oasis is a private home nestled in the Stoney Creek area of Wintergreen Resort. This 1.3 acre property ...

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  • The Wintergreen Treehouse
    Click For Pricing

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    The Wintergreen Treehouse

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Relax and enjoy your time secluded in nature on roughly four acres of land right down the road from Paul's Creek, many h ...

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  • Hot Tub & Views | Mid Century Modern Wonder
    From $654 per night (USD)

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    Hot Tub & Views | Mid Century Modern Wonder

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    15

    Welcome to this beautiful, mid-century modern mountain home! You will fall in love with the open floor plan, chef’s kitc ...

    From $654 per night (USD)

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  • Dream Big in the Blue Ridge Mountains
    From $1474 per night (USD)

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    Dream Big in the Blue Ridge Mountains

    Bedrooms:
    8
    Bathrooms:
    10
    Sleeps:
    25

    Bring everybody together in our Blue Ridge Mountain 10,000 square foot home. The home is located in Nellysford`s Stoney ...

    From $1474 per night (USD)

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  • The Blue Llama | Pets OK | Llama Loft | Fire Pit | Fenced Yard | Off Nelson 151
    From $302 per night (USD)

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    The Blue Llama | Pets OK | Llama Loft | Fire Pit | Fenced Yard | Off Nelson 151

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to our blue-tiful Blue Llama vacation rental located at the heart of Nelson County in Nellysford, Virginia. Insp ...

    From $302 per night (USD)

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  • Little Bear: 4br/ 4ba, mountain & valley view. Pet friendly!
    From $792 per night (USD)

    Expedia

    Little Bear: 4br/ 4ba, mountain & valley view. Pet friendly!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to Little Bear! We'd love to provide you with a comfortable stay and clear views so you can enjoy the beauty of ...

    From $792 per night (USD)

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  • Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
    From $331 per night (USD)

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    Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Nestled in the heart of Wintergreen, This charming slope side 2-bedroom/ 2-bath. (sleeps six) condo steps from the ski ...

    From $331 per night (USD)

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  • Cozy Wintergreen Ski Chalet -hot tub-Walk to slopes & family friendly!
    From $487 per night (USD)

    Expedia

    Cozy Wintergreen Ski Chalet -hot tub-Walk to slopes & family friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to "The Brown Bear Lodge", your year-round retreat in the heart of Wintergreen Ski Resort- just a short walk fro ...

    From $487 per night (USD)

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  • Mountain Inn Lodge 54 with Wintergreen Advantage
    From $297 per night (USD)

    VRBO

    Mountain Inn Lodge 54 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Pet-Friendly Loft Retreat Escape to the mountains in this cozy loft-style guest room at the Mountain Inn, ...

    From $297 per night (USD)

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  • - NEW - Spruce Creek Retreat
    From $206 per night (USD)

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    - NEW - Spruce Creek Retreat

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Relax with the whole family at this peaceful cottage nestled in the heart of the blue ridge mountains. Short distance to ...

    From $206 per night (USD)

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  • Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard
    From $438 per night (USD)

    VRBO

    Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    8min walk or 3min drive to ski. Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to ...

    From $438 per night (USD)

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  • Sleepy Bear Chalet
    From $194 per night (USD)

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    Sleepy Bear Chalet

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Escape to the mountains and enjoy your peace and quiet from the chaos of everyday life. Relax by the fire at night and s ...

    From $194 per night (USD)

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  • Enjoy all 4 seasons at this spacious, pet friendly home! Great views, sleeps 10
    From $577 per night (USD)

    VRBO

    Enjoy all 4 seasons at this spacious, pet friendly home! Great views, sleeps 10

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    You won’t be able to look away from the spectacular Shenandoah Valley and Blue Ridge mountain views offered by this Wint ...

    From $577 per night (USD)

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  • Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
    From $449 per night (USD)

    Expedia

    Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Welcome to the Mountain Treehouse! We recently renovated the home with all upgraded amenities, including a brand new hot ...

    From $449 per night (USD)

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  • Where the Trail Ends
    From $175 per night (USD)

    VRBO

    Where the Trail Ends

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Some trips are about doing everything. This one's about slowing down. Nestled inside Wintergreen Resort, this updated m ...

    From $175 per night (USD)

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  • Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
    From $424 per night (USD)

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    Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Updated 2 bedroom/2 bathroom slope-side condo with amazing mountain views. Short walk around the building gets you to ou ...

    From $424 per night (USD)

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  • Cozy Studio Overlooking 18 Hole
    From $193 per night (USD)

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    Cozy Studio Overlooking 18 Hole

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    A slice of paradise overlooking the 18th hole and Devils Grill. Located across the street from the spa and Nature Found ...

    From $193 per night (USD)

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  • Ski In & Out Mountain & Firework Views Studio
    From $225 per night (USD)

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    Ski In & Out Mountain & Firework Views Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy a stylish experience at this centrally-located studio next to the Mountain Inn. Our spacious deck overlooks the s ...

    From $225 per night (USD)

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  • BEARADISE “Glamping Paradise”
    From $207 per night (USD)

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    BEARADISE “Glamping Paradise”

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Pictures Don't Do this Justice. Private Adorable One Bedroom Glamping along a Mountain Creek. The space Amazing views of ...

    From $207 per night (USD)

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  • Bear Den Cottage
    From $401 per night (USD)

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    Bear Den Cottage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Cozy Cottage minutes from Lexington or minutes from The Parkway, Endless trails for hiking, hunting with Creek for fishi ...

    From $401 per night (USD)

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    Details