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Results: 902 Rentals

  • Wintergreen Resort Condo: Deck & Golf Course Views
    From $182 per night (USD)

    VRBO

    Wintergreen Resort Condo: Deck & Golf Course Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    On-Site Golf & Ski Storage | Covered Deck | Near Hiking Embark on a nature escape worth remembering at this 2-bedroom, ...

    From $182 per night (USD)

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  • Cozy Cute Condo in Wintergreen Resort
    From $183 per night (USD)

    Expedia

    Cozy Cute Condo in Wintergreen Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: This perfect little getaway is nestled into the hillside and centrally located within Wintergreen. Our place c ...

    From $183 per night (USD)

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    Details
  • Uncork and Unwind ! Perfect Mountain Retreat at Wintergreen Resort !
    From $230 per night (USD)

    VRBO

    Uncork and Unwind ! Perfect Mountain Retreat at Wintergreen Resort !

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Uncork and unwind Mountain Retreat Whether you are looking for a romantic getaway, a fun family trip or even just a pl ...

    From $230 per night (USD)

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  • Aftonshire Cottage - Heart of Afton's Wine Region
    From $270 per night (USD)

    Expedia

    Aftonshire Cottage - Heart of Afton's Wine Region

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Tucked away in the heart of Nelson County’s 151 Trail at the foot of the Blue Ridge Mountains, Aftonshire Cottage beckon ...

    From $270 per night (USD)

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  • \Glass & Pine\ Home close to Bold Rock & Vineyards
    From $378 per night (USD)

    VRBO

    \"Glass & Pine\" Home close to Bold Rock & Vineyards

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Nestled in the breathtaking Blue Ridge Mountains of Nellysford, VA, this newly built contemporary home is perfect for na ...

    From $378 per night (USD)

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    Details
  • Hot Tub | Fire Pit | River | State Park | King Bed
    From $251 per night (USD)

    Expedia

    Hot Tub | Fire Pit | River | State Park | King Bed

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome! 'Hygge' is a Danish-inspired concept that embraces the idea of all things warm and cozy. This home is delightfu ...

    From $251 per night (USD)

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  • The Distinguished Squirrel Chalet walking distance
    From $288 per night (USD)

    VRBO

    The Distinguished Squirrel Chalet walking distance

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Nestled at Wintergreen Resort, this unique Treeloft home is just steps from the slopes! Walking access just 4 houses dow ...

    From $288 per night (USD)

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    Details
  • 5 King Beds | Sleeps 18 | Game Room | Brew Trail
    From $809 per night (USD)

    Expedia

    5 King Beds | Sleeps 18 | Game Room | Brew Trail

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    18

    Welcome! This home is luxuriously spacious. With five king beds, a 3-bunk bunk room, and plenty of indoor and outdoor se ...

    From $809 per night (USD)

    Expedia

    Details
  • The Stay at The Wildland
    From $777 per night (USD)

    VRBO

    The Stay at The Wildland

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    16

    The Stay at The Wildland is a non-toxic, peaceful retreat for the whole family, bordered by the historic James River and ...

    From $777 per night (USD)

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  • Pickleball | 2 Homes | Sleeps 20 | 151 Brew Trail
    From $700 per night (USD)

    Expedia

    Pickleball | 2 Homes | Sleeps 20 | 151 Brew Trail

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    20

    Welcome! Nelly's Retreat is located in the lovely rolling hills of Nellysford, VA. The property includes two spacious ho ...

    From $700 per night (USD)

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    Details
  • Pickleball | 2 Master Suites | Fire Pit | Game Rm
    From $425 per night (USD)

    VRBO

    Pickleball | 2 Master Suites | Fire Pit | Game Rm

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Welcome! Nelly’s Oasis, a newly renovated garage with a modern interior, is comfortably situated in the foothills of the ...

    From $425 per night (USD)

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    Details
  • Pickleball | Sleeps 14 | 151 Brew Trail | Firepit
    From $435 per night (USD)

    Expedia

    Pickleball | Sleeps 14 | 151 Brew Trail | Firepit

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Welcome! Nelly's Chalet is right off the 151 Wine & Brew Trail. Take in the scenic windy roads, the rolling hills, roman ...

    From $435 per night (USD)

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    Details
  • Couple's Getaway in Stoney Creek at Wintergreen!
    From $236 per night (USD)

    VRBO

    Couple's Getaway in Stoney Creek at Wintergreen!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Private Location | Ideal Area for Hikers | Wraparound Deck | 15 Mi to Wintergreen Resort A romantic retreat awaits at t ...

    From $236 per night (USD)

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  • Charming 1-bedroom apt in beautiful Afton close to Breweries/Wineries & trails!
    From $151 per night (USD)

    Expedia

    Charming 1-bedroom apt in beautiful Afton close to Breweries/Wineries & trails!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Escape to this fabulous apartment in picturesque Afton. This adorable rental features 1 bedroom, 1 bath, full kitchen, W ...

    From $151 per night (USD)

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    Details
  • Castle Snow with Wintergreen Advantage
    From $652 per night (USD)

    VRBO

    Castle Snow with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    • 4 bedrooms- K, Q, D, TT • 3 bathrooms • Full- sized kitchen • Hot tub • 2181 square feet Offering beautiful year-roun ...

    From $652 per night (USD)

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  • The Cottage at Spindle Hill: an Artist’s Farm
    From $322 per night (USD)

    Expedia

    The Cottage at Spindle Hill: an Artist’s Farm

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Relax and unwind in this fabulous handcrafted cottage— every detail has been considered! Beautiful mountain setting on s ...

    From $322 per night (USD)

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    Details
  • the wooder house: charming haven in the woods, family-friendly & dog-friendly
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    the wooder house: charming haven in the woods, family-friendly & dog-friendly

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to the Wooder House, a private, comfortable home centered on 38 acres in the heart of Virginia's beautiful Nelso ...

    Click For Pricing

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  • Charming 2-bedroom tiny house close to hiking trails and Nelson 151
    From $268 per night (USD)

    Expedia

    Charming 2-bedroom tiny house close to hiking trails and Nelson 151

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    The Rockfish Tiny Home is Nestled in Central Virginia's picturesque countryside, this modern 500-sqft tiny home offers t ...

    From $268 per night (USD)

    Expedia

    Details
  • Entire house in Afton, VA. The Road House at Stumble Creek - 2 bedroom
    From $240 per night (USD)

    VRBO

    Entire house in Afton, VA. The Road House at Stumble Creek - 2 bedroom

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Your cozy Afton retreat awaits at this 2-bedroom house in the heart of Hwy 151 wine country. Views of the Appalachian Mo ...

    From $240 per night (USD)

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  • Walk to Ski Slopes: Wintergreen Resort ‘Treehouse’
    From $230 per night (USD)

    Expedia

    Walk to Ski Slopes: Wintergreen Resort ‘Treehouse’

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Short Walk to Eagle’s Swoop | Furnished Deck w/ Mountain View | Fireside Relaxation ‘Treehouse’ is an updated mountain ...

    From $230 per night (USD)

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  • Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.
    From $501 per night (USD)

    VRBO

    Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Your Wintergreen Resort adventure begins at this 5-bedroom house. With 1 king bed, 3 queen beds, and 4 twin beds, this p ...

    From $501 per night (USD)

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    Details
  • SECLUDED LAKE FRONT LOG CABIN
    From $275 per night (USD)

    VRBO

    SECLUDED LAKE FRONT LOG CABIN

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Located in the foothills of the Blue Ridge Mountains, just south of Charlottesville (about 20 minutes) you will find thi ...

    From $275 per night (USD)

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    Details
  • Unwind at Bear Pause, located right at Wintergreen Resort.
    From $382 per night (USD)

    VRBO

    Unwind at Bear Pause, located right at Wintergreen Resort.

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    11

    Bear Pause at Wintergreen Resort – Spacious Getaway for Family & Friends! Escape to the mountains and unwind at Bear Pa ...

    From $382 per night (USD)

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    Details
  • Unique Stay! Yurt with Mountain View, 1 min to Breweries & Hiking, 5 min to Lake
    From $195 per night (USD)

    Expedia

    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 $195 per night (USD)

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

    VRBO

    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)

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    Details
  • Mtn Views~Fire Pit~King Bed~Lake~Breweries 1 mi!
    From $512 per night (USD)

    Expedia

    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 $512 per night (USD)

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  • Charming 4-bedroom farmhouse in tranquil Lowesville with AC, WiFi
    From $306 per night (USD)

    VRBO

    Charming 4-bedroom farmhouse in tranquil Lowesville with AC, WiFi

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

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

    From $306 per night (USD)

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    Details
  • 2-bedroom condo in peaceful Wintergreen Resort with WiFi, fitness room
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    Expedia

    2-bedroom condo in peaceful Wintergreen Resort with WiFi, fitness room

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This 2-bedroom condo is perfect for your escape to Wintergreen Resort. The property offers a peaceful and soothing atmos ...

    Click For Pricing

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  • Overlook 180 degree views w/Peloton!
    From $288 per night (USD)

    VRBO

    Overlook 180 degree views w/Peloton!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Some of the best views at Wintergreen! Come and relax at our newly updated condo at Overlook! The master bedroom boasts ...

    From $288 per night (USD)

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    Details
  • Wow! What A View!
    From $239 per night (USD)

    Expedia

    Wow! What A View!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience the Beauty of Wintergreen Resort from Our Cozy Condo! Welcome to your perfect mountain getaway! Our recently ...

    From $239 per night (USD)

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  • Slopeside Serenity , For Graduation & Easter
    From $286 per night (USD)

    VRBO

    Slopeside Serenity , For Graduation & Easter

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This home has beautiful views of the ski slopes right off the back porch. With a large sectional couch in the living roo ...

    From $286 per night (USD)

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    Details
  • Altitude Adjustment for Hiking, Swimming, summer camps
    From $245 per night (USD)

    Expedia

    Altitude Adjustment for Hiking, Swimming, summer camps

    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 $245 per night (USD)

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  • Slopes @ Tyro
    From $786 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 $786 per night (USD)

    VRBO

    Details
  • Our Mountain Getaway, hiking, Swimming, summer camps
    From $963 per night (USD)

    Expedia

    Our Mountain Getaway, hiking, Swimming, summer camps

    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 $963 per night (USD)

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    Details
  • Cliffs Edge,Hike, Play & Splash into Summer! Camps too!
    From $454 per night (USD)

    VRBO

    Cliffs Edge,Hike, Play & Splash into Summer! Camps too!

    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 $454 per night (USD)

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  • Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
    From $209 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 $209 per night (USD)

    Expedia

    Details
  • Patio + Pool Access: Wintergreen Resort Getaway!
    From $186 per night (USD)

    VRBO

    Patio + Pool Access: Wintergreen Resort Getaway!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Fairway Woods Condos | In-Unit Laundry | Golf Course View Your next Virginia adventure awaits at this Wintergreen Resor ...

    From $186 per night (USD)

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  • Privacy and Views in Wintergreen
    From $446 per night (USD)

    VRBO

    Privacy and Views in Wintergreen

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    New listing! Welcome to our cozy Wintergreen home, located on one of the most private lots in the area. You'll truly fee ...

    From $446 per night (USD)

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    Details
  • Branch and Barrel: Hot Tub & Sauna + Mtn Views
    From $708 per night (USD)

    VRBO

    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 farmhou ...

    From $708 per night (USD)

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    Details
  • Experience the Magic at our Luxury 2 Bdrm, w/Majestic Blue Ridge Mountain Views
    From $95 per night (USD)

    Expedia

    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, Short term Contractors, Retreat Visito ...

    From $95 per night (USD)

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    Details
  • Modern Lakeside Mountain Retreat With Cabin Charm
    From $661 per night (USD)

    VRBO

    Modern Lakeside Mountain Retreat With Cabin Charm

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Escape to this stunning lakeside mountain retreat, nestled in a serene forest setting. This modern 5-bedroom, 3-bath hom ...

    From $661 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 $456 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 $456 per night (USD)

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    Details
  • Summer Music Festival - Luxe Cliff House Retreat
    From $385 per night (USD)

    VRBO

    Summer Music Festival - Luxe Cliff House Retreat

    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 $385 per night (USD)

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    Details
  • Blue Ridge Montebello Cabin 3
    From $161 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 $161 per night (USD)

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  • Scenic A-Frame Near Trails and Wineries
    From $638 per night (USD)

    VRBO

    Scenic A-Frame Near Trails and Wineries

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to Peak Retreat, a modern A-frame with mountain views near Skyline Drive, the Blue Ridge Parkway, and local winer ...

    From $638 per night (USD)

    VRBO

    Details
  • Blue Ridge Montebello Cabin 2
    From $198 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 $198 per night (USD)

    Expedia

    Details
  • Country Roads Take Me Home.
    From $180 per night (USD)

    VRBO

    Country Roads Take Me Home.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The Chimneys…. Ideal for the nature lover, hiker and adventure seeking individual looking for a truly rustic getaway. Fi ...

    From $180 per night (USD)

    VRBO

    Details
  • Pool Access: Scenic Condo in Wintergreen Resort!
    From $209 per night (USD)

    Expedia

    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 $209 per night (USD)

    Expedia

    Details
  • Wintergreen 5BR with Hot Tub, Sauna, Firepit
    From $543 per night (USD)

    VRBO

    Wintergreen 5BR with Hot Tub, Sauna, Firepit

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    New listing- welcome to Marigold on the Mountain! Located in the heart of Wintergreen, Marigold features a hot tub and c ...

    From $543 per night (USD)

    VRBO

    Details
  • Mountain Views, Hot Tub, Impeccable Design
    From $568 per night (USD)

    Expedia

    Mountain Views, Hot Tub, Impeccable Design

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    New listing! Welcome to Chasing Altitudes, a designer-decorated Wintergreen home with fantastic year-round views. The mu ...

    From $568 per night (USD)

    Expedia

    Details
  • New! Modern Luxe House Sleeps 20 + Pool + Spa + Firepit + Epic Views
    From $1768 per night (USD)

    VRBO

    New! Modern Luxe House Sleeps 20 + Pool + Spa + Firepit + Epic Views

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    20

    Welcome to The Lodge at Rock Spring Mountain Farm — a spacious 7-bedroom, 6.5-bath retreat with stunning mountain views. ...

    From $1768 per night (USD)

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    Details
  • Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
    From $182 per night (USD)

    Expedia

    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 $182 per night (USD)

    Expedia

    Details
  • Charming 2-bedroom condo in beautiful Wintergreen Resort
    From $202 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 $202 per night (USD)

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    Details
  • Home & Cottage Near Wintergreen Resort!
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    Expedia

    Home & Cottage Near Wintergreen Resort!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    2 Desk Workspaces w/ Printer | Free WiFi | 2 Fireplaces | Mountain View | 2,350 Sq Ft Bedroom 1: King Bed | Bedroom 2: ...

    Click For Pricing

    Expedia

    Details
  • Willow Haven: Cozy cabin in delightful Afton
    From $223 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 $223 per night (USD)

    VRBO

    Details
  • Faber Farmhouse: Hot Tub Near & Wineries/Breweries
    From $437 per night (USD)

    Expedia

    Faber Farmhouse: Hot Tub Near & Wineries/Breweries

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to Faber Farmhouse, conveniently located in Faber, VA with easy access to the Nelson 151 corridor, Charlottesvil ...

    From $437 per night (USD)

    Expedia

    Details
  • Mtn View at Swoopside Hideaway: Walk to Everything
    From $269 per night (USD)

    VRBO

    Mtn View at Swoopside Hideaway: Walk to Everything

    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 $269 per night (USD)

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    Details
  • Serene and secluded 4 Br/3ba Foxwood at Stoney Creek
    From $418 per night (USD)

    Expedia

    Serene and secluded 4 Br/3ba Foxwood at Stoney Creek

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Summer Specials – June, July & August! 🌿 Spacious 4BR/3BA home in Stoney Creek at Wintergreen on 1.4 peaceful acres. E ...

    From $418 per night (USD)

    Expedia

    Details
  • Newly Built Custom 3-Bedroom Retreat in Scenic Afton – AC & WiFi Included
    From $407 per night (USD)

    VRBO

    Newly Built Custom 3-Bedroom Retreat in Scenic Afton – AC & WiFi Included

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Afton is waiting for you at this secluded 3-bedroom cottage in Virginia's wine country. With 1 king bed and 2 queen beds ...

    From $407 per night (USD)

    VRBO

    Details
  • Mountain Views in Wintergreen
    From $463 per night (USD)

    Expedia

    Mountain Views in Wintergreen

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    New Listing- welcome to Dogwood Retreat! This spacious Wintergreen home features two levels of decks. On the upper deck, ...

    From $463 per night (USD)

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    Details
  • Brand new serene luxury cottage just off the Brew Ridge Trail
    From $181 per night (USD)

    VRBO

    Brand new serene luxury cottage just off the Brew Ridge Trail

    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 $181 per night (USD)

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    Details
  • Charming 4bedroom single story home in Wintergreen VA. 2Primary suites, flat lot
    From $749 per night (USD)

    Expedia

    Charming 4bedroom single story home in Wintergreen VA. 2Primary suites, flat lot

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Relax with the whole family at this peaceful getaway in Wintergreen Resort, VA. This single-story home features two prim ...

    From $749 per night (USD)

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  • Highridge 06 with Wintergreen Advantage
    From $358 per night (USD)

    VRBO

    Highridge 06 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    4

    Apartment style condominium with several location options: please indicate in Comments section if you have a preference ...

    From $358 per night (USD)

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  • Family-friendly 10-bedroom B&B near Wintergreen golf & ski. Great for groups!
    From $1053 per night (USD)

    Expedia

    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 $1053 per night (USD)

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    Details
  • Thrilling Views HotTub Sauna Gym EV Charger DogOK
    From $573 per night (USD)

    VRBO

    Thrilling Views HotTub Sauna Gym EV Charger DogOK

    Bedrooms:
    7
    Bathrooms:
    5
    Sleeps:
    10

    Sweeping panoramic view of Blue Ridge Mountains year round. Retreats, romantic weekends or adventurous getaways. Close t ...

    From $573 per night (USD)

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    Details
  • Wintergreen Resort Eagles Court Condo Ski in Ski out
    From $363 per night (USD)

    Expedia

    Wintergreen Resort Eagles Court Condo Ski in Ski out

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Experience Wintergreen Resort like a local in this 3-bedroom slopeside condo. With a king bed, queen bed, and bunk bed, ...

    From $363 per night (USD)

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    Details
  • Wintergreen Luxury, Breathtaking Views
    From $1087 per night (USD)

    VRBO

    Wintergreen Luxury, Breathtaking Views

    Bedrooms:
    5
    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 $1087 per night (USD)

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    Details
  • Secluded Cabin– Pool w/ Mountain Views + Trails
    From $584 per night (USD)

    Expedia

    Secluded Cabin– Pool w/ Mountain Views + Trails

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Nestled in Lovingston, this delightful cabin offers amazing views, firepit and in-ground pool. 4 cozy bedrooms with a mi ...

    From $584 per night (USD)

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  • Timbers Lodge 31 with Wintergreen Advantage
    From $349 per night (USD)

    VRBO

    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 $349 per night (USD)

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    Details
  • Mountain Inn Lodge 77 with Wintergreen Advantage
    From $293 per night (USD)

    Expedia

    Mountain Inn Lodge 77 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Loft style guest room located in the Mountain Inn near the Blackrock Village Center and walkable to the ski slopes and R ...

    From $293 per night (USD)

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    Details
  • Oh Deer NEW LUXURY-renovated, hot tub/sauna, views
    From $1069 per night (USD)

    VRBO

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

    Bedrooms:
    6
    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 $1069 per night (USD)

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  • Updated Mtn House 2 Mins to Resort: 3King Beds, HotTub, Game room, Family & Pets
    From $774 per night (USD)

    Expedia

    Updated Mtn House 2 Mins to Resort: 3King Beds, HotTub, Game room, Family & Pets

    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 $774 per night (USD)

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  • Timbers Studio 48 With Wintergreen Advantage
    From $215 per night (USD)

    VRBO

    Timbers Studio 48 With Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Hotel style guest room located in the Timbers complex near the Blackrock Village Center and walkable to the ski slopes a ...

    From $215 per night (USD)

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    Details
  • NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort
    From $598 per night (USD)

    Expedia

    NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

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

    From $598 per night (USD)

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    Details
  • Brand new 3-bedroom house at the base of the Blue Ridge Mountains
    From $397 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 $397 per night (USD)

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    Details
  • Dobie 36  with Wintergreen Advantage
    From $943 per night (USD)

    Expedia

    Dobie 36 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Located in the Dobie condominium complex, near the Blackrock Village Center and walkable to the ski slopes and Resort di ...

    From $943 per night (USD)

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    Details
  • Dobie 48  with Wintergreen Advantage
    From $942 per night (USD)

    VRBO

    Dobie 48 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Located in the Dobie condominium complex, near the Blackrock Village Center and walkable to the ski slopes and Resort di ...

    From $942 per night (USD)

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    Details
  • Walk to Wintergreen. Hot Tub. Hiking off Property. Cozy 4 BR home.
    From $392 per night (USD)

    Expedia

    Walk to Wintergreen. Hot Tub. Hiking off Property. Cozy 4 BR home.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Perfect getaway for all seasons! Families, girls trips, get-togethers, couples retreats. Walk to the Resort, Dining, and ...

    From $392 per night (USD)

    Expedia

    Details
  • Mntn View Hot Tub Foosball Fireplace Multi-Deck
    From $425 per night (USD)

    VRBO

    Mntn View Hot Tub Foosball Fireplace Multi-Deck

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    About this space Adventure and relaxation await at this mountain top Wintergreen Resort home! With 4 bedrooms and 4.5 ba ...

    From $425 per night (USD)

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    Details
  • Wintergreen Grandeur
    From $1123 per night (USD)

    Expedia

    Wintergreen Grandeur

    Bedrooms:
    10
    Bathrooms:
    9
    Sleeps:
    18

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

    From $1123 per night (USD)

    Expedia

    Details
  • Elegant- 4 Outdoor Areas, Massage, Hot Tub, Sauna, Fam Friendly, Game Room, View
    From $946 per night (USD)

    VRBO

    Elegant- 4 Outdoor Areas, Massage, Hot Tub, Sauna, Fam Friendly, Game Room, View

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    18

    NEW! Escape to Chateau Greenstone, the Wintergreen retreat with plenty for EVERYONE. 3 game areas for kids of all ages ( ...

    From $946 per night (USD)

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    Details
  • Timbers 11 With Wintergreen Advantage
    From $267 per night (USD)

    Expedia

    Timbers 11 With Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in the Timbers complex near the Blackrock Village Center and walkable to the ski slopes and Resort dining. Bedro ...

    From $267 per night (USD)

    Expedia

    Details
  • Three Ridges 05 With Wintergreen Advantage
    From $403 per night (USD)

    VRBO

    Three Ridges 05 With Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in the Three Ridges condominium complex, near the Blackrock Village Center and walkable to the ski slopes and Re ...

    From $403 per night (USD)

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    Details
  • Lofty Pursuits: Spectacular View + EV Charger
    From $275 per night (USD)

    Expedia

    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 $275 per night (USD)

    Expedia

    Details
  • Laurelwood Hollow: Walk to Ski & Swim
    From $222 per night (USD)

    VRBO

    Laurelwood Hollow: Walk to Ski & Swim

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Laurelwood Hollow is a 2 bedroom, 2 bath condo located within Wintergreen Resort. It's just a short walk to the slopes, ...

    From $222 per night (USD)

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    Details
  • New Build! Log Cabin with Hot Tub in Wintergreen
    From $533 per night (USD)

    Expedia

    New Build! Log Cabin with Hot Tub in Wintergreen

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    15

    New listing! Welcome to Loggin' Off, a log cabin built in 2024 in the heart of Wintergreen. This 6 bedroom home sleeps 1 ...

    From $533 per night (USD)

    Expedia

    Details
  • Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!
    From $294 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 $294 per night (USD)

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    Details
  • Luxury 1-BR Suite near Nelson 151 | Pet-Friendly!
    From $214 per night (USD)

    Expedia

    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 $214 per night (USD)

    Expedia

    Details
  • Pet-Friendly King Suite w/ Desk & Smart Entry
    From $218 per night (USD)

    VRBO

    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 $218 per night (USD)

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    Details
  • Amazing Mountain Views, Hot Tub and Close to Wineries and Breweries
    From $384 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 $384 per night (USD)

    VRBO

    Details
  • Walk to Slopes: Wintergreen Resort Condo w/ Pool
    From $218 per night (USD)

    VRBO

    Walk to Slopes: Wintergreen Resort Condo w/ Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Next to the Wintergreen Resort Market | Ski Closet | Walk to Conference Center Get ready for mountain fun at this 2-bed ...

    From $218 per night (USD)

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    Details
  • Three Ridges 27 With Wintergreen Advantage
    From $539 per night (USD)

    Expedia

    Three Ridges 27 With Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Located in the Three Ridges condominium complex, near the Blackrock Village Center and walkable to the ski slopes and Re ...

    From $539 per night (USD)

    Expedia

    Details
  • Three Ridges 64 With Wintergreen Advantage
    From $385 per night (USD)

    VRBO

    Three Ridges 64 With Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in the Three Ridges condominium complex, near the Blackrock Village Center and walkable to the ski slopes and Re ...

    From $385 per night (USD)

    VRBO

    Details
  • Modern & cozy 2 bed, 2 bath condo at Wintergreen Resort
    From $250 per night (USD)

    Expedia

    Modern & cozy 2 bed, 2 bath condo at Wintergreen Resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Weller’s Retreat at Stone Ridge is a modern yet cozy 2 bed, 2 bath condo at Wintergreen Resort. Enjoy a fully equipped k ...

    From $250 per night (USD)

    Expedia

    Details
  • Antlers Aweigh with Wintergreen Advantage
    From $655 per night (USD)

    VRBO

    Antlers Aweigh with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Antlers Aweigh is a cozy mountain retreat facing east towards the Rockfish Valley. Enjoy morning coffee and sunrise view ...

    From $655 per night (USD)

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    Details
  • Serenity Cabin-3 Bedroom Woodland Retreat in Wintergreen
    From $289 per night (USD)

    VRBO

    Serenity Cabin-3 Bedroom Woodland Retreat in Wintergreen

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $289 per night (USD)

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    Details
  • Northridge 07 With Wintergreen Advantage
    From $231 per night (USD)

    VRBO

    Northridge 07 With Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Located in the Northridge condominium complex in the Devils Knob area with close proximity to The Spa, Aquatics and Fitn ...

    From $231 per night (USD)

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    Details
  • Serenity Slope with Wintergreen Advantage
    From $575 per night (USD)

    Expedia

    Serenity Slope with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Serenity Slope! Our cozy cabin in the woods offers many opportunities for adventure and relaxation. Enter int ...

    From $575 per night (USD)

    Expedia

    Details
  • Dobie 24 with Wintergreen Advantage
    From $955 per night (USD)

    VRBO

    Dobie 24 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Located in the Dobie condominium complex, near the Blackrock Village Center and walkable to the ski slopes and Resort di ...

    From $955 per night (USD)

    VRBO

    Details
  • Wintergreen Ski Resort: Waterfall Hikes, Bike, Fish, Spa, Pool, Wineries and Bre
    From $402 per night (USD)

    Expedia

    Wintergreen Ski Resort: Waterfall Hikes, Bike, Fish, Spa, Pool, Wineries and Bre

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

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

    From $402 per night (USD)

    Expedia

    Details