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Results: 890 Rentals

  • Highridge Court 30 with Wintergreen Advantage
    From $299 per night (USD)

    VRBO

    Highridge Court 30 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

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

    From $299 per night (USD)

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    Details
  • Cliffs 20 with Wintergreen Advantage
    From $537 per night (USD)

    Expedia

    Cliffs 20 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $537 per night (USD)

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    Details
  • Dobie 43 with Wintergreen Advantage
    From $308 per night (USD)

    VRBO

    Dobie 43 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $308 per night (USD)

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    Details
  • Dobie 04 with Wintergreen Advantage
    From $319 per night (USD)

    Expedia

    Dobie 04 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $319 per night (USD)

    Expedia

    Details
  • Highridge Place 42 with Wintergreen Advantage
    From $413 per night (USD)

    VRBO

    Highridge Place 42 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $413 per night (USD)

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    Details
  • White Oak 51 with Wintergreen Advantage
    From $464 per night (USD)

    Expedia

    White Oak 51 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Located in the White Oak condominium complex, near the Blackrock Village Center, ski slopes and Resort dining. Bedroom 1 ...

    From $464 per night (USD)

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    Details
  • Three Ridges 59 with Wintergreen Advantage
    From $318 per night (USD)

    VRBO

    Three Ridges 59 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 $318 per night (USD)

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    Details
  • Laurelwood 98 with Wintergreen Advantage
    From $220 per night (USD)

    Expedia

    Laurelwood 98 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in the Laurelwood condominium complex, near the Blackrock Village Center and walkable to the ski slopes and Reso ...

    From $220 per night (USD)

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    Details
  • Cliffs 27 with Wintergreen Advantage
    From $410 per night (USD)

    VRBO

    Cliffs 27 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $410 per night (USD)

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    Details
  • Mountain Inn Lodge 65 with Wintergreen Advantage
    From $250 per night (USD)

    Expedia

    Mountain Inn Lodge 65 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 $250 per night (USD)

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    Details
  • Three Ridges 15 with Wintergreen Advantage
    From $537 per night (USD)

    VRBO

    Three Ridges 15 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 $537 per night (USD)

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    Details
  • Overlook 43 with Wintergreen Advantage
    From $410 per night (USD)

    Expedia

    Overlook 43 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $410 per night (USD)

    Expedia

    Details
  • Dobie 16 with Wintergreen Advantage
    From $313 per night (USD)

    VRBO

    Dobie 16 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $313 per night (USD)

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    Details
  • Fairway Woods 01 with Wintergreen Advantage
    From $374 per night (USD)

    Expedia

    Fairway Woods 01 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $374 per night (USD)

    Expedia

    Details
  • Laurelwood 12 with Wintergreen Advantage
    From $299 per night (USD)

    VRBO

    Laurelwood 12 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in the Laurelwood condominium complex, near the Blackrock Village Center and walkable to the ski slopes and Reso ...

    From $299 per night (USD)

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    Details
  • Stoneridge 43 with Wintergreen Advantage
    From $278 per night (USD)

    Expedia

    Stoneridge 43 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

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

    From $278 per night (USD)

    Expedia

    Details
  • Eagles Court 27 with Wintergreen Advantage
    From $310 per night (USD)

    VRBO

    Eagles Court 27 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $310 per night (USD)

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    Details
  • Stoneridge 77 with Wintergreen Advantage
    From $278 per night (USD)

    Expedia

    Stoneridge 77 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

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

    From $278 per night (USD)

    Expedia

    Details
  • Overlook 41 with Wintergreen Advantage
    From $410 per night (USD)

    VRBO

    Overlook 41 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $410 per night (USD)

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    Details
  • Mountain Inn Lodge 76 with Wintergreen Advantage
    From $250 per night (USD)

    Expedia

    Mountain Inn Lodge 76 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 $250 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 70 with Wintergreen Advantage
    From $250 per night (USD)

    VRBO

    Mountain Inn Lodge 70 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 $250 per night (USD)

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    Details
  • Mountain Inn Lodge 64 with Wintergreen Advantage
    From $250 per night (USD)

    Expedia

    Mountain Inn Lodge 64 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 $250 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 71 with Wintergreen Advantage
    From $250 per night (USD)

    VRBO

    Mountain Inn Lodge 71 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 $250 per night (USD)

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    Details
  • Mountain Inn Lodge 82 with Wintergreen Advantage
    From $250 per night (USD)

    Expedia

    Mountain Inn Lodge 82 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 $250 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 59 with Wintergreen Advantage
    From $250 per night (USD)

    VRBO

    Mountain Inn Lodge 59 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 $250 per night (USD)

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    Details
  • Mountain Inn Lodge 83 with Wintergreen Advantage
    From $250 per night (USD)

    Expedia

    Mountain Inn Lodge 83 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 $250 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 60 with Wintergreen Advantage
    From $250 per night (USD)

    VRBO

    Mountain Inn Lodge 60 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 $250 per night (USD)

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    Details
  • Three Ridges 74 with Wintergreen Advantage
    From $299 per night (USD)

    Expedia

    Three Ridges 74 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 $299 per night (USD)

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    Details
  • Three Ridges 90 with Wintergreen Advantage
    From $299 per night (USD)

    VRBO

    Three Ridges 90 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 $299 per night (USD)

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    Details
  • 3 min drive to slopes and hiking right in the neighborhood! Sleeps 8!
    From $247 per night (USD)

    Expedia

    3 min drive to slopes and hiking right in the neighborhood! Sleeps 8!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    Welcome to our spacious two-story townhome with enough room to enjoy your family and also escape when you are sick of th ...

    From $247 per night (USD)

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    Details
  • Majestic Mtn Cabin w quick hiking access & short distance to overlook!
    From $328 per night (USD)

    VRBO

    Majestic Mtn Cabin w quick hiking access & short distance to overlook!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    You have found the PERFECT Family-Friendly Wintergreen Getaway! ⨇Fully-remodeled luxurious 2000sq ft ski chalet ⨇Brief w ...

    From $328 per night (USD)

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  • Tanners Ridge 14 with Wintergreen Advantage
    From $284 per night (USD)

    Expedia

    Tanners Ridge 14 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in the Tanners Ridge condominium complex in the Devils Knob area with close proximity to The Spa, Aquatics and F ...

    From $284 per night (USD)

    Expedia

    Details
  • Highlands 48 with Wintergreen Advantage
    From $410 per night (USD)

    VRBO

    Highlands 48 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $410 per night (USD)

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    Details
  • Gumtree #5 with Wintergreen Advantage
    From $378 per night (USD)

    Expedia

    Gumtree #5 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $378 per night (USD)

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    Details
  • Saddleback Sanctuary: Indoor Pool + beside Veritas
    From $1343 per night (USD)

    VRBO

    Saddleback Sanctuary: Indoor Pool + beside Veritas

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    FIRST FLOOR (Entry Floor): LIVING ROOM - Large living room with seating for your entire group, smart TV, and balcony acc ...

    From $1343 per night (USD)

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    Details
  • Retreat @ 3 Ridges \/ 3min->Slopes  \/ Walk to Dining
    From $303 per night (USD)

    Expedia

    Retreat @ 3 Ridges \/ 3min->Slopes \/ Walk to Dining

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to The Retreat at Three Ridges! Our cozy, Scandinavian-inspired condo is your perfect Blue Ridge Mountain getawa ...

    From $303 per night (USD)

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    Details
  • Cozy Wintergreen Condo
    From $177 per night (USD)

    VRBO

    Cozy Wintergreen Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to our charming condo nestled in the heart of Wintergreen, where outdoor adventure meets relaxation. This cozy tw ...

    From $177 per night (USD)

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    Details
  • Art & Soul: Luxury Mtn Retreat\/Sauna & Hot Tub
    From $742 per night (USD)

    Expedia

    Art & Soul: Luxury Mtn Retreat\/Sauna & Hot Tub

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Art & Soul, a stunning vacation rental nestled in the picturesque mountains of Wintergreen, Virginia. This en ...

    From $742 per night (USD)

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    Details
  • View With a Room │ Mountain Home in Wine Country
    From $335 per night (USD)

    VRBO

    View With a Room │ Mountain Home in Wine Country

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to the View with a Room! Nestled at the base of Afton mountain, this 3 bed, 2 bath, house is close to trails, w ...

    From $335 per night (USD)

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    Details
  • Game Room & Fire Pit: Wintergreen Resort Home!
    From $352 per night (USD)

    Expedia

    Game Room & Fire Pit: Wintergreen Resort Home!

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    9

    Pets Welcome w/ Fee | 3 Living Areas | Well-Stocked Kitchen | Seasonal Community Pool Access Year-round outdoor adventu ...

    From $352 per night (USD)

    Expedia

    Details
  • Art & Soul Guest House: Mtn Views + Hot Tub
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    VRBO

    Art & Soul Guest House: Mtn Views + Hot Tub

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Please note: * Art and Soul Guest House may not suitable for toddlers due to open spaces between stairs and an electric ...

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  • Ridge Retreat @ Wintergreen!
    From $499 per night (USD)

    Expedia

    Ridge Retreat @ Wintergreen!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Top of the Mountain! Enjoy a view of the slopes and a backdrop view of many miles beyond that. You will want to wake up ...

    From $499 per night (USD)

    Expedia

    Details
  • Blue Rivers Cottage and Loft
    From $393 per night (USD)

    VRBO

    Blue Rivers Cottage and Loft

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    The accommodation features a spacious and inviting 3-bedroom, 2-bathroom home with an open floor plan that seamlessly co ...

    From $393 per night (USD)

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    Details
  • Sycamore Shade: 151 House, HOT TUB, Mountain Views
    From $281 per night (USD)

    Expedia

    Sycamore Shade: 151 House, HOT TUB, Mountain Views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sycamore Shade is a one-level home with comfortable private rooms and engaging community spaces. The house is accessible ...

    From $281 per night (USD)

    Expedia

    Details
  • Blue Rivers Cottage with Mountain Views
    From $267 per night (USD)

    VRBO

    Blue Rivers Cottage with Mountain Views

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    One level living space. Spacious, open floor plan with a sitting room, open kitchen/dining room and family room with TV. ...

    From $267 per night (USD)

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    Details
  • Blue Rivers Loft on the Brew Ridge Trail
    From $130 per night (USD)

    Expedia

    Blue Rivers Loft on the Brew Ridge Trail

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Located near the famous Route 151, the area is surrounded by popular breweries and vineyards, offering plenty of options ...

    From $130 per night (USD)

    Expedia

    Details
  • Luxury Home w\/Mountain Views, Hot Tub, EV Charger, Play Equipment
    From $896 per night (USD)

    VRBO

    Luxury Home w\/Mountain Views, Hot Tub, EV Charger, Play Equipment

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    11

    Summary: Luxurious and spacious, this home offers views of the famous Humpback Rocks ridges, from just about every room. ...

    From $896 per night (USD)

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    Details
  • Afton Awaits: Pool & Hot Tub\/Central to Wineries
    From $671 per night (USD)

    Expedia

    Afton Awaits: Pool & Hot Tub\/Central to Wineries

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Nestled in the picturesque hills of Afton, Virginia, this luxury modern farmhouse offers the perfect blend of rustic cha ...

    From $671 per night (USD)

    Expedia

    Details
  • Spacious 5 bedroom modern home with mountain views galore.  Sauna + EV charger.
    From $722 per night (USD)

    VRBO

    Spacious 5 bedroom modern home with mountain views galore. Sauna + EV charger.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to Altitude Adjustment!! The whole group will love this spacious and unique space. In the heart of the "Brew R ...

    From $722 per night (USD)

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    Details
  • Aftonshire Cottage - Heart of Afton's Wine Region
    From $293 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 $293 per night (USD)

    Expedia

    Details
  • Serene haven \The Nest\ in Wintergreen, close to activities and restaurants.
    From $164 per night (USD)

    VRBO

    Serene haven \"The Nest\" in Wintergreen, close to activities and restaurants.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    A warm space to relax and recharge. Close to it all or simply do nothing. Near hiking, golf, the slopes, tennis, spa and ...

    From $164 per night (USD)

    VRBO

    Details
  • Ski Chalet at Wintergreen Resort with Amazing Views!
    From $300 per night (USD)

    Expedia

    Ski Chalet at Wintergreen Resort with Amazing Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    Escape to this charming 2- bedroom , 2 bathroom condo located in The Highlands at Wintergreen Resort, the perfect retre ...

    From $300 per night (USD)

    Expedia

    Details
  • Cozy Cabin on Cub Creek: Near Wintergreen & AT
    From $185 per night (USD)

    VRBO

    Cozy Cabin on Cub Creek: Near Wintergreen & AT

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cub Creek is a secluded cozy mountain cabin located only minutes away from Devil's Backbone, Wintergreen Ski Resort, the ...

    From $185 per night (USD)

    VRBO

    Details
  • *NEW* Mountain View Vista: Resort Condo w\/ Views
    From $290 per night (USD)

    Expedia

    *NEW* Mountain View Vista: Resort Condo w\/ Views

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    The condo's main features are as described: KITCHEN: Newly renovated and fully stocked with a fridge, dishwasher, oven ...

    From $290 per night (USD)

    Expedia

    Details
  • 6-bedroom house in Nellysford with WiFi AC Skiing Tubing and Golf
    From $566 per night (USD)

    VRBO

    6-bedroom house in Nellysford with WiFi AC Skiing Tubing and Golf

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    Discover the beauty of Nellysford from this 6-bedroom house. Marvelous king and queen beds await you, ensuring a brillia ...

    From $566 per night (USD)

    VRBO

    Details
  • Close to the Slopes - 2min - Large Private Hot Tub
    From $539 per night (USD)

    Expedia

    Close to the Slopes - 2min - Large Private Hot Tub

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Escape to this charming 4-bedroom cabin just 0.4 miles from the slopes of Wintergreen Resort. Whether you're here to ski ...

    From $539 per night (USD)

    Expedia

    Details
  • Red White & WTG: Game Room + Hot Tub
    From $1039 per night (USD)

    VRBO

    Red White & WTG: Game Room + Hot Tub

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    16

    Welcome to Red, White and Wintergreen! Escape to the scenic beauty of Wintergreen Resort in Virginia with this spacious ...

    From $1039 per night (USD)

    VRBO

    Details
  • Spacious Cabin in the Woods near Breweries and Wineries
    From $484 per night (USD)

    Expedia

    Spacious Cabin in the Woods near Breweries and Wineries

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Escape to the Treetops Lodge, your own "cabin in the woods." Located on 12 acres of lush mountainside, the Treetops Lod ...

    From $484 per night (USD)

    Expedia

    Details
  • Charming 2-bedroom condo in delightful Wintergreen Resort with AC, WiFi
    From $259 per night (USD)

    VRBO

    Charming 2-bedroom condo in delightful Wintergreen Resort with AC, WiFi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy a peaceful stay at this delightful, updated 2-bedroom condo in Wintergreen Resort. The cozy bedrooms each feature ...

    From $259 per night (USD)

    VRBO

    Details
  • 2 Homes | Sleeps 20 | Game Rooms | 151 Brew Trail
    From $742 per night (USD)

    Expedia

    2 Homes | Sleeps 20 | Game Rooms | 151 Brew Trail

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    20

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

    From $742 per night (USD)

    Expedia

    Details
  • 2 Master Suites | Brew Trail | Fire Pit | Game Rm
    From $364 per night (USD)

    VRBO

    2 Master Suites | Brew Trail | Fire Pit | Game Rm

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

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

    From $364 per night (USD)

    VRBO

    Details
  • Sleeps 14 | 151 Brew Trail | Game RM | Firepit
    From $401 per night (USD)

    Expedia

    Sleeps 14 | 151 Brew Trail | Game RM | Firepit

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

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

    From $401 per night (USD)

    Expedia

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

    VRBO

    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 $525 per night (USD)

    Expedia

    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 $525 per night (USD)

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    Details
  • The Cottage at Spindle Hill: an Artist’s Farm
    From $312 per night (USD)

    VRBO

    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 $312 per night (USD)

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  • Spindle Hill Farm’s School House ~ EV\/ pond
    From $341 per night (USD)

    Expedia

    Spindle Hill Farm’s School House ~ EV\/ pond

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Charming & Historic 1932 School House on Spindle Hill Farm sleeps 6 with private ponds 🐟 views of the Blue Ridge Mounta ...

    From $341 per night (USD)

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    Details
  • Charming 2-bedroom tiny house with hot tub, fire-pit and surrounded by wineries
    From $264 per night (USD)

    VRBO

    Charming 2-bedroom tiny house with hot tub, fire-pit and surrounded by wineries

    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 $264 per night (USD)

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    Details
  • Walk to Ski Slopes: Wintergreen Resort ‘Treehouse’
    From $277 per night (USD)

    Expedia

    Walk to Ski Slopes: Wintergreen Resort ‘Treehouse’

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

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

    From $277 per night (USD)

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  • Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.
    From $355 per night (USD)

    VRBO

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

    Bedrooms:
    5
    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 $355 per night (USD)

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    Details
  • Charming 4-bedroom farmhouse in tranquil Lowesville with AC, WiFi
    From $374 per night (USD)

    Expedia

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

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    7

    Stay comfortably in Lowesville at this 4-bedroom farmhouse. With a full dining room and eat-in kitchen, there is plenty ...

    From $374 per night (USD)

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    Details
  • SECLUDED LAKE FRONT LOG CABIN
    From $258 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 $258 per night (USD)

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    Details
  • Unwind at Bear Pause, located right at Wintergreen Resort.
    From $535 per night (USD)

    Expedia

    Unwind at Bear Pause, located right at Wintergreen Resort.

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    11

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

    From $535 per night (USD)

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    Details
  • Hawthorne Cabin ~ NEW ~ Romantic ~ Unique ~ Serene
    From $182 per night (USD)

    Expedia

    Hawthorne Cabin ~ NEW ~ Romantic ~ Unique ~ Serene

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Escape to this charming 1-bedroom cabin nestled in the heart of Nellysford, VA. Surrounded by lush forests and stunning ...

    From $182 per night (USD)

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    Details
  • Unique Stay! Yurt with Mountain View, 1 min to Breweries & Hiking, 5 min to Lake
    From $261 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 $261 per night (USD)

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    Details
  • Overlook 180 degree views w\/Peloton!
    From $309 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 $309 per night (USD)

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    Details
  • You'll say \Wow!\ Over This View!
    From $436 per night (USD)

    Expedia

    You'll say \"Wow!\" Over This 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 $436 per night (USD)

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    Details
  • Slopeside Serenity , For Graduation & Easter
    From $250 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 $250 per night (USD)

    VRBO

    Details
  • Altitude Adjustment for Memorial weekend and summer camps
    From $240 per night (USD)

    Expedia

    Altitude Adjustment for Memorial weekend and 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 $240 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, For Graduation & Easter
    From $1022 per night (USD)

    Expedia

    Our Mountain Getaway, For Graduation & Easter

    Bedrooms:
    6
    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 $1022 per night (USD)

    Expedia

    Details
  • Cliffs Edge,Hike, Play & Splash into Summer! Camps too!
    From $427 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 $427 per night (USD)

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    Details
  • Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
    From $189 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 $189 per night (USD)

    Expedia

    Details
  • Patio + Pool Access: Wintergreen Resort Getaway!
    From $222 per night (USD)

    VRBO

    Patio + Pool Access: Wintergreen Resort Getaway!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

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

    From $222 per night (USD)

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  • Privacy and Views in Wintergreen
    From $492 per night (USD)

    Expedia

    Privacy and Views in Wintergreen

    Bedrooms:
    4
    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 $492 per night (USD)

    Expedia

    Details
  • NEW LISTING! Cozy retreat with Mountain Views, Hiking &  Ski-Out @ Tyro
    From $367 per night (USD)

    VRBO

    NEW LISTING! Cozy retreat with Mountain Views, Hiking & Ski-Out @ Tyro

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Tequila Sunrise! Located slope-side at Tequila and Lower Tyro, our home offers a true ski-in/ski-out experien ...

    From $367 per night (USD)

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    Details
  • Entire house in Afton, VA. The Road House at Stumble Creek - 2 bedroom
    From $237 per night (USD)

    Expedia

    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 $237 per night (USD)

    Expedia

    Details
  • TENNIS # GOLF # HOT TUB
    From $487 per night (USD)

    VRBO

    TENNIS # GOLF # HOT TUB

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Spring is here at Wintergreen! Plan your tennis or golf weekend. Enjoy brand new 4 person hot tub! This Beautiful Hom ...

    From $487 per night (USD)

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    Details
  • Wren Time, Wintergreen Mountain Retreat with Hot Tub
    From $421 per night (USD)

    Expedia

    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 $421 per night (USD)

    Expedia

    Details
  • Authentic Log Cabin-
    From $296 per night (USD)

    VRBO

    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 $296 per night (USD)

    VRBO

    Details
  • Insane Mountain Views - New Listing
    From $1558 per night (USD)

    Expedia

    Insane Mountain Views - New Listing

    Bedrooms:
    10
    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 $1558 per night (USD)

    Expedia

    Details
  • Gorgeous countryside farmhouse on 10 acres. Carriage house also available.
    From $530 per night (USD)

    VRBO

    Gorgeous countryside farmhouse on 10 acres. Carriage house also available.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Experience tranquil, country farm living with beautiful vistas from back & front porches as well as the sunroom and pati ...

    From $530 per night (USD)

    VRBO

    Details
  • Stunning Views, Hot Tub, Impeccable Design
    From $519 per night (USD)

    Expedia

    Stunning Views, Hot Tub, Impeccable Design

    Bedrooms:
    4
    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 $519 per night (USD)

    Expedia

    Details
  • Ski-In\/Ski-Out Comfy Condo
    From $131 per night (USD)

    VRBO

    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 $131 per night (USD)

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    Details
  • Moose Lodge\/Great for Families\/Walk to Slopes\/Hot Tub\/Pool Table\/Fire Pit
    From $492 per night (USD)

    VRBO

    Moose Lodge\/Great for Families\/Walk to Slopes\/Hot Tub\/Pool Table\/Fire Pit

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    15

    Our spacious chalet in Wintergreen Resort is approximately, a 10-minute walk to the ski slopes on the next street over. ...

    From $492 per night (USD)

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  • Pet Friendly Cozy Mountain Retreat-sleeps 10!
    From $348 per night (USD)

    VRBO

    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 $348 per night (USD)

    VRBO

    Details
  • The Refuge at Laurel
    From $161 per night (USD)

    Expedia

    The Refuge at Laurel

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy a cozy mountain getaway located in the heart of Nelson County. Perfect for couples, friends, or singles, the Refug ...

    From $161 per night (USD)

    Expedia

    Details
  • Modern Wintergreen Cabin with Hot Tub, Sauna
    From $573 per night (USD)

    VRBO

    Modern Wintergreen Cabin with Hot Tub, Sauna

    Bedrooms:
    5
    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 $573 per night (USD)

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    Details
  • Cozy Country small two bedroom home.
    From $246 per night (USD)

    Expedia

    Cozy Country small two bedroom home.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Relax with the whole family at this peaceful country home. Cozy small home that you can sit back at the firepit or play ...

    From $246 per night (USD)

    Expedia

    Details
  • Newly remodeled farmhouse on 151 Trail in Nelson County
    From $279 per night (USD)

    VRBO

    Newly remodeled farmhouse on 151 Trail in Nelson County

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $279 per night (USD)

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    Details
  • Restored Vintage Airstream at Craft Brewery
    From $304 per night (USD)

    Expedia

    Restored Vintage Airstream at Craft Brewery

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located just a short walk from our Basecamp Brewpub, this restored vintage Airstream is the perfect home base for explor ...

    From $304 per night (USD)

    Expedia

    Details