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Results: 819 Rentals

  • Unique Stay! Yurt with Mountain View, 1 min to Breweries & Hiking, 5 min to Lake
    From $217 per night (USD)

    VRBO

    Unique Stay! Yurt with Mountain View, 1 min to Breweries & Hiking, 5 min to Lake

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Come for a memorable stay at the Rockfish Valley Yurt and enjoy "glamping" at its finest! Picturesque mountain views a ...

    From $217 per night (USD)

    VRBO

    Details
  • Cozy dog- friendly condo that sleeps 6 -with pools and VIEWS, minutes to slopes
    From $256 per night (USD)

    Expedia

    Cozy dog- friendly condo that sleeps 6 -with pools and VIEWS, minutes to slopes

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to a tranquil 2-bedroom condo at Wintergreen Resort! This well appointed property offers a perfect place for unw ...

    From $256 per night (USD)

    Expedia

    Details
  • Mtn Views~Fire Pit~King Bed~Lake~Breweries 1 mi!
    From $409 per night (USD)

    VRBO

    Mtn Views~Fire Pit~King Bed~Lake~Breweries 1 mi!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    About this space The Blue Ridge Cabin is on the 151 Brew-ridge Trail at the base of the mountain, mins to wineries, brew ...

    From $409 per night (USD)

    VRBO

    Details
  • Spacious home for relaxation in Roseland.  30 min from hiking trails, wineries.
    From $348 per night (USD)

    VRBO

    Spacious home for relaxation in Roseland. 30 min from hiking trails, wineries.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Stay peacefully in Roseland at this 4-bedroom farmhouse on a working cattle and sheep farm. With a full dining room and ...

    From $348 per night (USD)

    VRBO

    Details
  • Overlook 180 degree views w/Peloton!
    From $444 per night (USD)

    VRBO

    Overlook 180 degree views w/Peloton!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy some of the best views at Wintergreen from this updated Overlook condo. Take in beautiful sunrises from the privat ...

    From $444 per night (USD)

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    Details
  • Altitude Adjustment-It's Pumpkin Spice Time!
    From $240 per night (USD)

    Expedia

    Altitude Adjustment-It's Pumpkin Spice Time!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This is a newly renovated condo with new flooring and furniture . Great place to come and relax after a day of hiking, ...

    From $240 per night (USD)

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  • Slopes @ Tyro
    From $456 per night (USD)

    VRBO

    Slopes @ Tyro

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    We have a spacious, slope side, 3 level home with a convenient ski out basement. The resort & its surrounding areas offe ...

    From $456 per night (USD)

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    Details
  • Our Mountain Getaway
    From $674 per night (USD)

    Expedia

    Our Mountain Getaway

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    Come make Our Mountain Getaway your own! This is a very private home surrounded by beautiful mountain views with lots of ...

    From $674 per night (USD)

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    Details
  • Cliffs Edge-A Contemporary Mountain Home
    From $494 per night (USD)

    VRBO

    Cliffs Edge-A Contemporary Mountain Home

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredi ...

    From $494 per night (USD)

    VRBO

    Details
  • Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
    From $299 per night (USD)

    Expedia

    Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Escape to this cozy condo in Wintergreen Resort. The sunrises are spectacular and the views glorious! This charming prop ...

    From $299 per night (USD)

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  • Privacy and Views in Wintergreen
    From $427 per night (USD)

    VRBO

    Privacy and Views in Wintergreen

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    Welcome to our cozy Wintergreen home, located on one of the most private lots in the area. You'll truly feel at peace wi ...

    From $427 per night (USD)

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    Details
  • Branch and Barrel: Hot Tub & Sauna + Mtn Views
    From $743 per night (USD)

    Expedia

    Branch and Barrel: Hot Tub & Sauna + Mtn Views

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Welcome to Branch and Barrel, the perfect quiet getaway right off the Nelson 151 Brew Trail. This stunning 1891 farmh ...

    From $743 per night (USD)

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    Details
  • Experience the Magic at our Luxury 2 Bdrm, w/Majestic Blue Ridge Mountain Views
    From $88 per night (USD)

    VRBO

    Experience the Magic at our Luxury 2 Bdrm, w/Majestic Blue Ridge Mountain Views

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    TERRIFIC place for Traveling Health Care Professionals, Relocating Professionals, Digital Nomads, Short term Contractors ...

    From $88 per night (USD)

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    Details
  • The Moose Lodge-Hot Tub/Game Room/Fire Pit/Grill/Walk to Slopes-0.7mi to Lodge
    From $658 per night (USD)

    VRBO

    The Moose Lodge-Hot Tub/Game Room/Fire Pit/Grill/Walk to Slopes-0.7mi to Lodge

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Welcome to The Moose Lodge at Wintergreen – Your Mountain Escape Awaits! Gather your family and friends and make unforg ...

    From $658 per night (USD)

    VRBO

    Details
  • WTG Luxe Cliff House Retreat: Hike, Sip, Relax
    From $363 per night (USD)

    VRBO

    WTG Luxe Cliff House Retreat: Hike, Sip, Relax

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Discover the perfect getaway at Boho Cliff House, a stunning 3BR, 2BA home nestled in the heart of Wintergreen Resort. I ...

    From $363 per night (USD)

    VRBO

    Details
  • Blue Ridge Montebello Cabin 3
    From $211 per night (USD)

    Expedia

    Blue Ridge Montebello Cabin 3

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Discover the beauty of Montebello from this cozy 1-bedroom cabin. The bedroom features a comfortable queen bed, perfect ...

    From $211 per night (USD)

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    Details
  • Escape to a modern A-frame retreat with mountain views, a hot tub, cozy cinema lounge, and easy access to Nelson 151, Shenandoah National Park, hiking trails, wineries, and breweries.
    From $609 per night (USD)

    VRBO

    Escape to a modern A-frame retreat with mountain views, a hot tub, cozy cinema lounge, and easy access to Nelson 151, Shenandoah National Park, hiking trails, wineries, and breweries.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to Peak Retreat, a luxury A-frame perched high above the Blue Ridge Mountains with sweeping panoramic views and a ...

    From $609 per night (USD)

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    Details
  • Blue Ridge Montebello Cabin 2
    From $227 per night (USD)

    Expedia

    Blue Ridge Montebello Cabin 2

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Consider this charming cabin your home away from home while you visit Montebello. With 2 cozy bedrooms featuring a king ...

    From $227 per night (USD)

    Expedia

    Details
  • Pool Access: Scenic Condo in Wintergreen Resort!
    From $286 per night (USD)

    VRBO

    Pool Access: Scenic Condo in Wintergreen Resort!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Year-Round Mountain Retreat | Seasonal Shuttle to Lift | Blue Ridge Backdrop Mornings come with a view at this Wintergr ...

    From $286 per night (USD)

    VRBO

    Details
  • Wintergreen 5BR with Hot Tub, Sauna, Firepit
    From $1043 per night (USD)

    Expedia

    Wintergreen 5BR with Hot Tub, Sauna, Firepit

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Welcome to Marigold on the Mountain! Located in the heart of Wintergreen, Marigold features a hot tub and cedar barrel s ...

    From $1043 per night (USD)

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    Details
  • Mountain Views, Hot Tub, Impeccable Design
    From $1132 per night (USD)

    VRBO

    Mountain Views, Hot Tub, Impeccable Design

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    Welcome to Chasing Altitudes, a designer-decorated Wintergreen home with fantastic year-round views. The multiple decks ...

    From $1132 per night (USD)

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    Details
  • Modern Luxe House Hot Tub 20ppl
    From $1473 per night (USD)

    Expedia

    Modern Luxe House Hot Tub 20ppl

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    20

    Escape to this luxurious 7BR/6.5BA farmhouse retreat, perfectly nestled in the heart of the Blue Ridge Mountains. With s ...

    From $1473 per night (USD)

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    Details
  • Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
    From $273 per night (USD)

    VRBO

    Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wake up to the fresh mountain air in a condo on the edge of the mountain. The most breathtaking sunrises and views of th ...

    From $273 per night (USD)

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    Details
  • Charming 2-bedroom condo in beautiful Wintergreen Resort
    From $321 per night (USD)

    VRBO

    Charming 2-bedroom condo in beautiful Wintergreen Resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Your family will be close to everything when you stay at this centrally-located retreat. Nestled in the sought after Wi ...

    From $321 per night (USD)

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    Details
  • Willow Haven: Cozy cabin in delightful Afton
    From $252 per night (USD)

    VRBO

    Willow Haven: Cozy cabin in delightful Afton

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Consider this cabin your home away from home while you visit Afton. Nestled in the heart of this enchanting city, our we ...

    From $252 per night (USD)

    VRBO

    Details
  • Faber Farmhouse: Hot Tub Near & Wineries/Breweries
    From $621 per night (USD)

    Expedia

    Faber Farmhouse: Hot Tub Near & Wineries/Breweries

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    🛌 Sleeps 9 | 💦 NEW Hot Tub | 🍷🍺 Central to Wineries & Breweries Below is a breakdown of the 3-story, newly-renovate ...

    From $621 per night (USD)

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    Details
  • Prime WTG Location - Summer Fun at Swoopside Hideaway - Outdoor Pools
    From $231 per night (USD)

    VRBO

    Prime WTG Location - Summer Fun at Swoopside Hideaway - Outdoor Pools

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Stay at the heart of Wintergreen Resort at Swoopside Hideaway, a wonderful 2BR, 1.5BA condo perched right on the Eagles ...

    From $231 per night (USD)

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    Details
  • Foxwood at Stoney Creek • Wintergreen + Wine Trail Base • Mtn Views
    From $574 per night (USD)

    VRBO

    Foxwood at Stoney Creek • Wintergreen + Wine Trail Base • Mtn Views

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Spacious 4BR/3BA home in Stoney Creek at Wintergreen on 1.4 peaceful acres. Enjoy a screened-in porch with skylights and ...

    From $574 per night (USD)

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    Details
  • Mountain Views in Wintergreen
    From $394 per night (USD)

    VRBO

    Mountain Views in Wintergreen

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    Welcome to Dogwood Retreat! This spacious Wintergreen home features two levels of decks. On the upper deck, you'll love ...

    From $394 per night (USD)

    VRBO

    Details
  • Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
    From $169 per night (USD)

    Expedia

    Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Your cozy getaway awaits in Afton at this marvelous cottage. With 1 queen bed, WiFi, heating, and a hair dryer, guests w ...

    From $169 per night (USD)

    Expedia

    Details
  • Wintergreen Mountain Top Escape: Steps to Golf, Hiking & High-Country Views
    From $392 per night (USD)

    VRBO

    Wintergreen Mountain Top Escape: Steps to Golf, Hiking & High-Country Views

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    • Things to know (we want you to relax, not waste your time!) • 4 bedrooms (sleeps 10) • 3 Full baths • No pets • Yes, v ...

    From $392 per night (USD)

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    Details
  • Highridge 06 with Wintergreen Advantage
    From $507 per night (USD)

    Expedia

    Highridge 06 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Highridge Mountain Getaway Enjoy a relaxing mountain escape in this 2-bedroom, 2-bath condo in the Highridge community ...

    From $507 per night (USD)

    Expedia

    Details
  • Family-friendly 10-bedroom B&B near Wintergreen golf & ski. Great for groups!
    From $1090 per night (USD)

    VRBO

    Family-friendly 10-bedroom B&B near Wintergreen golf & ski. Great for groups!

    Bedrooms:
    3
    Bathrooms:
    10
    Sleeps:
    24

    Located 30 miles south of Charlottesville, VA, Acorn Inn is a convenient rendezvous spot between northern and southern s ...

    From $1090 per night (USD)

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  • Wintergreen Luxury, Breathtaking Views
    From $799 per night (USD)

    Expedia

    Wintergreen Luxury, Breathtaking Views

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    16

    Welcome to Stargazer, one of Wintergreen's premier properties. The views are second-to-none throughout the home, and esp ...

    From $799 per night (USD)

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    Details
  • Secluded Mountain Cabin Firepit 12ppl
    From $457 per night (USD)

    VRBO

    Secluded Mountain Cabin Firepit 12ppl

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    In the heart of Fortune’s Cove, surrounded by 800 acres of hiking trails, this secluded mountain home offers the perfect ...

    From $457 per night (USD)

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    Details
  • Timbers Lodge 31 with Wintergreen Advantage
    From $336 per night (USD)

    Expedia

    Timbers Lodge 31 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    First floor slope side unit with walkout ski in and ski out access. Located in the Timbers complex near the Blackrock Vi ...

    From $336 per night (USD)

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  • Mountain Inn Lodge 77 with Wintergreen Advantage
    From $297 per night (USD)

    VRBO

    Mountain Inn Lodge 77 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn King Bed Loft Retreat Make your Wintergreen stay comfortable and convenient in this cozy loft-style guest ...

    From $297 per night (USD)

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  • Oh Deer NEW LUXURY-renovated, hot tub/sauna, views
    From $1308 per night (USD)

    VRBO

    Oh Deer NEW LUXURY-renovated, hot tub/sauna, views

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    18

    OH DEER! Welcome to your perfect escape in the Blue Ridge Mountains! Nestled just steps from the slopes of Wintergreen ...

    From $1308 per night (USD)

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  • Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
    From $973 per night (USD)

    VRBO

    Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    16

    Welcome to The Wintergreen Cozy! Reconnect and unwind in this 5-bed, 3-bath mountain retreat, perfect for large/multipl ...

    From $973 per night (USD)

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    Details
  • Timbers Studio 48 With Wintergreen Advantage
    From $267 per night (USD)

    Expedia

    Timbers Studio 48 With Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Mountain Retreat Make yourself at home in this inviting hotel-style guest room at the Timbers complex, ...

    From $267 per night (USD)

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  • NEW Warren’s Woods! Lovely 5BD, 3BA Wintergreen home. Hot Tub! NEW SPRING RATES!
    From $738 per night (USD)

    VRBO

    NEW Warren’s Woods! Lovely 5BD, 3BA Wintergreen home. Hot Tub! NEW SPRING RATES!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Wintergreen Resort is waiting for you at this 5-bedroom house. Each room offers an unique sleeping experience, from a ki ...

    From $738 per night (USD)

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  • Brand new 3-bedroom house at the base of the Blue Ridge Mountains
    From $440 per night (USD)

    VRBO

    Brand new 3-bedroom house at the base of the Blue Ridge Mountains

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Bucolic and chic— Take in all Nelson County’s Rockfish River Valley and “Brew Ridge Trail” (Rt. 151) have to offer in th ...

    From $440 per night (USD)

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  • Dobie 36  with Wintergreen Advantage
    From $731 per night (USD)

    VRBO

    Dobie 36 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Dobie Cozy Mountain Escape Enjoy a memorable mountain getaway in this inviting 3-bedroom, 3-bath condo at Dobie, conven ...

    From $731 per night (USD)

    VRBO

    Details
  • Dobie 48  with Wintergreen Advantage
    From $731 per night (USD)

    Expedia

    Dobie 48 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Dobie Spacious Mountain Retreat Escape to Wintergreen in this spacious 3-bedroom, 3-bath condo at Dobie, ideally locate ...

    From $731 per night (USD)

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  • Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard
    From $343 per night (USD)

    VRBO

    Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Escape to this cozy four-season mountain retreat tucked away on a private wooded lot in the heart of Wintergreen Resort. ...

    From $343 per night (USD)

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    Details
  • Mntn View Hot Tub Foosball Fireplace Multi-Deck
    From $520 per night (USD)

    Expedia

    Mntn View Hot Tub Foosball Fireplace Multi-Deck

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    4min drive to Wintergreen skiing. Adventure and relaxation await at this mountain top Wintergreen Resort home! With 4 be ...

    From $520 per night (USD)

    Expedia

    Details
  • Dragon's Back, 9BR 10BA in Wintergreen
    From $2082 per night (USD)

    VRBO

    Dragon's Back, 9BR 10BA in Wintergreen

    Bedrooms:
    10
    Bathrooms:
    9
    Sleeps:
    18

    Welcome to Dragon’s Back, one of Virginia's premier mountain chalets. With 6200 sq ft and some of the best views in the ...

    From $2082 per night (USD)

    VRBO

    Details
  • Luxe Wellness+Family Fun • Hot Tub|Massage Chair|Sauna|3 Game Rooms|Heated Patio
    From $1259 per night (USD)

    Expedia

    Luxe Wellness+Family Fun • Hot Tub|Massage Chair|Sauna|3 Game Rooms|Heated Patio

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    18

    Escape to Chateau Greenstone, the Wintergreen retreat where wellness & family fun shine. Something for EVERYONE: Adults ...

    From $1259 per night (USD)

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  • Timbers 11 With Wintergreen Advantage
    From $354 per night (USD)

    VRBO

    Timbers 11 With Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers One-Bedroom King Condo Enjoy a relaxing mountain retreat in this inviting one-bedroom condo at the Timbers, con ...

    From $354 per night (USD)

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    Details
  • Three Ridges 05 With Wintergreen Advantage
    From $465 per night (USD)

    Expedia

    Three Ridges 05 With Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Three Ridges Ski-Access Retreat Enjoy a comfortable mountain getaway in this 2-bedroom, 2-bath condo in the Three Ridge ...

    From $465 per night (USD)

    Expedia

    Details
  • Lofty Pursuits: Spectacular View + EV Charger
    From $420 per night (USD)

    VRBO

    Lofty Pursuits: Spectacular View + EV Charger

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Loft Pursuits! This cliff-hanging cabin amidst arboreal oasis featuring deck with view of Three Ridges. Unwin ...

    From $420 per night (USD)

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    Details
  • Three Little Bears: Walk to Ski & Swim
    From $310 per night (USD)

    Expedia

    Three Little Bears: Walk to Ski & Swim

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FIRST FLOOR: LIVING ROOM - NEW sectional sofa, smart TV, wood-burning fireplace (firewood provided), board gams and ki ...

    From $310 per night (USD)

    Expedia

    Details
  • New Build! Log Cabin with Hot Tub in Wintergreen
    From $467 per night (USD)

    VRBO

    New Build! Log Cabin with Hot Tub in Wintergreen

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    15

    Welcome to Loggin' Off, a log cabin built in 2024 in the heart of Wintergreen. This 6 bedroom home sleeps 15 and feature ...

    From $467 per night (USD)

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    Details
  • Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!
    From $317 per night (USD)

    VRBO

    Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Bring the whole family or your friends to this cozy cabin with lots of room for fun and relaxation. Check out the local ...

    From $317 per night (USD)

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    Details
  • Luxury 1-BR Suite near Nelson 151 | Pet-Friendly!
    From $168 per night (USD)

    VRBO

    Luxury 1-BR Suite near Nelson 151 | Pet-Friendly!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Experience upscale comfort in this 1-bedroom retreat featuring a king bed, queen sleeper sofa, full kitchen, and private ...

    From $168 per night (USD)

    VRBO

    Details
  • Pet-Friendly King Suite w/ Desk & Smart Entry
    From $168 per night (USD)

    Expedia

    Pet-Friendly King Suite w/ Desk & Smart Entry

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Experience laid-back comfort in this inviting 1-bedroom suite featuring a king bed, queen sleeper sofa, and an in-suite ...

    From $168 per night (USD)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Wintergreen Condo w/ Pool: Near Hike & Market!
    From $216 per night (USD)

    Expedia

    Wintergreen Condo w/ Pool: Near Hike & Market!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Walk to Wintergreen Conference Center | Near Hiking Trails | Community Pool Access Experience the best of the mountains ...

    From $216 per night (USD)

    Expedia

    Details
  • Three Ridges 27 With Wintergreen Advantage
    From $604 per night (USD)

    VRBO

    Three Ridges 27 With Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Three Ridges Charming Mountain Escape Make yourself at home in this charming 3-bedroom, 2-bath condo at Three Ridges, i ...

    From $604 per night (USD)

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  • Three Ridges 64 With Wintergreen Advantage
    From $339 per night (USD)

    Expedia

    Three Ridges 64 With Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Three Ridges Mountain Getaway Escape to the mountains in this 1-bedroom, 1-bath condo in Three Ridges at Wintergreen Re ...

    From $339 per night (USD)

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    Details
  • Treetop Mountain Escape - Fireplace, Views & Pool
    From $225 per night (USD)

    VRBO

    Treetop Mountain Escape - Fireplace, Views & Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wake up above the treetops in this beautifully updated top-floor condo at Wintergreen Resort — Virginia’s premier four-s ...

    From $225 per night (USD)

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  • Antlers Aweigh with Wintergreen Advantage
    From $643 per night (USD)

    Expedia

    Antlers Aweigh with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Antlers Aweigh is located above a Wintergreen hiking trail, making this home a great launch pad for all your mountain ad ...

    From $643 per night (USD)

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    Details
  • 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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    Details
  • Northridge 07 With Wintergreen Advantage
    From $339 per night (USD)

    Expedia

    Northridge 07 With Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Retreat in Northridge Escape to the mountains in this 1-bedroom, 2-bath condo in Northridge, located in Winter ...

    From $339 per night (USD)

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    Details
  • Dobie 24 with Wintergreen Advantage
    From $731 per night (USD)

    VRBO

    Dobie 24 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Dobie Spacious Mountain Getaway Experience a relaxing Wintergreen getaway in this spacious 3-bedroom, 3-bath condo at D ...

    From $731 per night (USD)

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    Details
  • Almost Heaven
    From $676 per night (USD)

    Expedia

    Almost Heaven

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    7

    Summary: Welcome to 'Almost Heaven"! A cozy, A-frame in the heart of Wintergreen Resort. This 3-bedroom, 3-bath retrea ...

    From $676 per night (USD)

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    Details
  • Trail Magic- Sk-in & Ski-out
    From $555 per night (USD)

    VRBO

    Trail Magic- Sk-in & Ski-out

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Summary: Trail Magic | Ski-In/Ski-Out Lodge at Wintergreen Resort with Hot Tub Experience the magic of the mountain ...

    From $555 per night (USD)

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    Details
  • All Downhill From Here
    From $239 per night (USD)

    VRBO

    All Downhill From Here

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    <p>Enjoy everything you need atop Virginia's <strong>Wintergreen Resort</strong>. This newly renovated condominium is lo ...

    From $239 per night (USD)

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    Details
  • Highlands 24 with Wintergreen Advantage
    From $667 per night (USD)

    VRBO

    Highlands 24 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Highlands Spacious Mountain Retreat Escape to the peaceful mountain setting of this spacious 3-bedroom, 3-bath condo in ...

    From $667 per night (USD)

    VRBO

    Details
  • Gum Tree #1 with Wintergreen Advantage
    From $338 per night (USD)

    Expedia

    Gum Tree #1 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Relaxing Mountain Escape at Wintergreen Resort Enjoy a peaceful getaway in this 1-bedroom, 1-bath condo at Wintergreen ...

    From $338 per night (USD)

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    Details
  • Wintergreen Luxury, Best Views in VA!
    From $1204 per night (USD)

    VRBO

    Wintergreen Luxury, Best Views in VA!

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    16

    Welcome to Blackrock Manor, a one-of-a-kind luxury chalet in Wintergreen that sleeps 16. Experience spectacular mountain ...

    From $1204 per night (USD)

    VRBO

    Details
  • Ledges   66 with Wintergreen Advantage
    From $507 per night (USD)

    Expedia

    Ledges 66 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Ledges Mountain Getaway Make yourself at home in this 2-bedroom, 2-bath condo in Ledges, nestled in Wintergreen's sceni ...

    From $507 per night (USD)

    Expedia

    Details
  • Vistas 87  with Wintergreen Advantage
    From $359 per night (USD)

    VRBO

    Vistas 87 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Vistas Cozy Mountain Escape Enjoy a peaceful getaway in this 1-bedroom, 2-bath condo in Vistas, nestled in Wintergreen' ...

    From $359 per night (USD)

    VRBO

    Details
  • Vistas 75  with Wintergreen Advantage
    From $360 per night (USD)

    Expedia

    Vistas 75 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Vistas Mountain Retreat Escape to the mountains in this 1-bedroom, 2-bath condo in Vistas, located in Wintergreen's sce ...

    From $360 per night (USD)

    Expedia

    Details
  • Overlook 08  with Wintergreen Advantage
    From $501 per night (USD)

    VRBO

    Overlook 08 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Overlook Mountain Getaway Unwind in this 2-bedroom, 2-bath condo in Overlook at Wintergreen Resort, nestled in the scen ...

    From $501 per night (USD)

    VRBO

    Details
  • 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)

    VRBO

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

    VRBO

    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)

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • 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)

    Expedia

    Details
  • Cool Mountain Breezes on The Slopes- It's Pumpkin Spice Time!
    From $341 per night (USD)

    VRBO

    Cool Mountain Breezes on The Slopes- It's Pumpkin Spice Time!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Your Wintergreen Resort adventure begins at this marvelous 3-bedroom home with a 2-levels of decks. With 2 king beds, 2 ...

    From $341 per night (USD)

    VRBO

    Details
  • Mountain Inn Studio 93 with Wintergreen Advantage
    From $284 per night (USD)

    Expedia

    Mountain Inn Studio 93 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Main-Floor King Retreat Enjoy a stylish and comfortable stay in this hotel-style guest room on the main fl ...

    From $284 per night (USD)

    Expedia

    Details
  • 4 Bedroom mountain cabin in the relaxing Wintergreen Resort with AC & Fireplace
    From $527 per night (USD)

    VRBO

    4 Bedroom mountain cabin in the relaxing Wintergreen Resort with AC & Fireplace

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Heaven on 11 is a comfortable 4 BR / 3 BA house with 3 Queen Beds, and a Twin trundle bed, sleeps 8, with two bedrooms o ...

    From $527 per night (USD)

    VRBO

    Details
  • Newly Built Designer Home in Wintergreen
    From $419 per night (USD)

    Expedia

    Newly Built Designer Home in Wintergreen

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Welcome to Onyx Hill, a custom built 4-bedroom, 3.5-bathroom home nestled within the picturesque Wintergreen Resort! Eve ...

    From $419 per night (USD)

    Expedia

    Details
  • The Snow House New Hot Tub Pet Friendly Creek PacMan
    From $646 per night (USD)

    VRBO

    The Snow House New Hot Tub Pet Friendly Creek PacMan

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    13

    Hot Tub Coming Dec. 2025*** We added a beautiful 8 seater hot tub for our deck overlooking the serene deck and creek be ...

    From $646 per night (USD)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • 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)

    VRBO

    Details
  • 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)

    VRBO

    Details
  • Ledges 50 with Wintergreen Advantage
    From $360 per night (USD)

    VRBO

    Ledges 50 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Ledges Mountain Escape Enjoy a peaceful retreat in this 1-bedroom, 1-bath condo in Ledges, nestled in Wintergreen's sce ...

    From $360 per night (USD)

    VRBO

    Details
  • Incredible Cabin with Beautiful Indoor and Outdoor Living Spaces in Virginia
    From $374 per night (USD)

    Expedia

    Incredible Cabin with Beautiful Indoor and Outdoor Living Spaces in Virginia

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to your perfect escape at this incredible resort in VA! Just 3 minutes from the ski slopes and snow tubing, our ...

    From $374 per night (USD)

    Expedia

    Details
  • Summer Golf - Walk to Ski | Sleeps 12 | Pets OK
    From $594 per night (USD)

    VRBO

    Summer Golf - Walk to Ski | Sleeps 12 | Pets OK

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    ✨ Luxury Wintergreen Retreat | Stoney Creek Golf Access | Ski, Golf, Pet-Friendly | Sleeps 12 Escape to the mountains a ...

    From $594 per night (USD)

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  • Charming Cabin Rental near Wineries and Hiking Trails in Afton, Virginia
    From $650 per night (USD)

    Expedia

    Charming Cabin Rental near Wineries and Hiking Trails in Afton, Virginia

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to our home away from home in the rolling hills of Afton, VA! We love to experience new restaurants, wineries, b ...

    From $650 per night (USD)

    Expedia

    Details