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Results: 807 Rentals

  • Stoneridge 56 with Wintergreen Advantage
    From $367 per night (USD)

    VRBO

    Stoneridge 56 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $367 per night (USD)

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    Details
  • Laurelwood 73 with Wintergreen Advantage
    From $403 per night (USD)

    Expedia

    Laurelwood 73 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $403 per night (USD)

    Expedia

    Details
  • Vistas 64 with Wintergreen Advantage
    From $404 per night (USD)

    VRBO

    Vistas 64 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $404 per night (USD)

    VRBO

    Details
  • Laurelwood 80 with Wintergreen Advantage
    From $403 per night (USD)

    Expedia

    Laurelwood 80 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $403 per night (USD)

    Expedia

    Details
  • Northridge 03 with Wintergreen Advantage
    From $370 per night (USD)

    VRBO

    Northridge 03 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $370 per night (USD)

    VRBO

    Details
  • Eagles Court 05 with Wintergreen Advantage
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    Expedia

    Eagles Court 05 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    Click For Pricing

    Expedia

    Details
  • Stoneridge Woods 05 with Wintergreen Advantage
    From $363 per night (USD)

    VRBO

    Stoneridge Woods 05 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $363 per night (USD)

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    Details
  • Overlook 26 with Wintergreen Advantage
    From $398 per night (USD)

    Expedia

    Overlook 26 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 $398 per night (USD)

    Expedia

    Details
  • Fairway Woods 43 with Wintergreen Advantage
    From $366 per night (USD)

    VRBO

    Fairway Woods 43 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 $366 per night (USD)

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    Details
  • Highridge Court 19 with Wintergreen Advantage
    From $536 per night (USD)

    Expedia

    Highridge Court 19 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $536 per night (USD)

    Expedia

    Details
  • Fairway Woods 22 with Wintergreen Advantage
    From $367 per night (USD)

    VRBO

    Fairway Woods 22 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 $367 per night (USD)

    VRBO

    Details
  • Stoneridge 75 with Wintergreen Advantage
    From $366 per night (USD)

    Expedia

    Stoneridge 75 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $366 per night (USD)

    Expedia

    Details
  • Eagles Court 19 with Wintergreen Advantage
    From $441 per night (USD)

    VRBO

    Eagles Court 19 with Wintergreen Advantage

    Bedrooms:
    1
    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 $441 per night (USD)

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    Details
  • Laurelwood 25 with Wintergreen Advantage
    From $404 per night (USD)

    Expedia

    Laurelwood 25 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $404 per night (USD)

    Expedia

    Details
  • Laurelwood 43 with Wintergreen Advantage
    From $403 per night (USD)

    VRBO

    Laurelwood 43 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $403 per night (USD)

    VRBO

    Details
  • Vistas 82 with Wintergreen Advantage
    From $542 per night (USD)

    Expedia

    Vistas 82 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $542 per night (USD)

    Expedia

    Details
  • Highridge Court 36 with Wintergreen Advantage
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    Expedia

    Highridge Court 36 with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

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

    Click For Pricing

    Expedia

    Details
  • White Oak 46 with Wintergreen Advantage
    From $481 per night (USD)

    Expedia

    White Oak 46 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 $481 per night (USD)

    Expedia

    Details
  • Highlands 17 with Wintergreen Advantage
    From $278 per night (USD)

    VRBO

    Highlands 17 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $278 per night (USD)

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    Details
  • Highridge Court 30 with Wintergreen Advantage
    From $273 per night (USD)

    Expedia

    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 $273 per night (USD)

    Expedia

    Details
  • Cliffs 20 with Wintergreen Advantage
    From $538 per night (USD)

    VRBO

    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 $538 per night (USD)

    VRBO

    Details
  • Dobie 43 with Wintergreen Advantage
    From $448 per night (USD)

    Expedia

    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 $448 per night (USD)

    Expedia

    Details
  • Dobie 04 with Wintergreen Advantage
    From $437 per night (USD)

    VRBO

    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 $437 per night (USD)

    VRBO

    Details
  • Highridge Place 42 with Wintergreen Advantage
    From $400 per night (USD)

    Expedia

    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 $400 per night (USD)

    Expedia

    Details
  • White Oak 51 with Wintergreen Advantage
    From $478 per night (USD)

    VRBO

    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 $478 per night (USD)

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    Details
  • Three Ridges 59 with Wintergreen Advantage
    From $404 per night (USD)

    Expedia

    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 $404 per night (USD)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Cliffs 27 with Wintergreen Advantage
    From $400 per night (USD)

    Expedia

    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 $400 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 65 with Wintergreen Advantage
    From $229 per night (USD)

    VRBO

    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 $229 per night (USD)

    VRBO

    Details
  • Three Ridges 15 with Wintergreen Advantage
    From $542 per night (USD)

    Expedia

    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 $542 per night (USD)

    Expedia

    Details
  • Overlook 43 with Wintergreen Advantage
    From $407 per night (USD)

    VRBO

    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 $407 per night (USD)

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    Details
  • Dobie 16 with Wintergreen Advantage
    From $437 per night (USD)

    Expedia

    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 $437 per night (USD)

    Expedia

    Details
  • Fairway Woods 01 with Wintergreen Advantage
    From $367 per night (USD)

    VRBO

    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 $367 per night (USD)

    VRBO

    Details
  • Laurelwood 12 with Wintergreen Advantage
    From $277 per night (USD)

    Expedia

    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 $277 per night (USD)

    Expedia

    Details
  • Stoneridge 43 with Wintergreen Advantage
    From $259 per night (USD)

    VRBO

    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 $259 per night (USD)

    VRBO

    Details
  • Eagles Court 27 with Wintergreen Advantage
    From $441 per night (USD)

    Expedia

    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 $441 per night (USD)

    Expedia

    Details
  • Stoneridge 77 with Wintergreen Advantage
    From $258 per night (USD)

    VRBO

    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 $258 per night (USD)

    VRBO

    Details
  • Overlook 41 with Wintergreen Advantage
    From $400 per night (USD)

    Expedia

    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 $400 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 76 with Wintergreen Advantage
    From $227 per night (USD)

    VRBO

    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 $227 per night (USD)

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    Details
  • Mountain Inn Lodge 70 with Wintergreen Advantage
    From $229 per night (USD)

    Expedia

    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 $229 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 64 with Wintergreen Advantage
    From $223 per night (USD)

    VRBO

    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 $223 per night (USD)

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    Details
  • Mountain Inn Lodge 71 with Wintergreen Advantage
    From $229 per night (USD)

    Expedia

    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 $229 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 82 with Wintergreen Advantage
    From $229 per night (USD)

    VRBO

    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 $229 per night (USD)

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    Details
  • Mountain Inn Lodge 59 with Wintergreen Advantage
    From $230 per night (USD)

    Expedia

    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 $230 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 83 with Wintergreen Advantage
    From $229 per night (USD)

    VRBO

    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 $229 per night (USD)

    VRBO

    Details
  • Mountain Inn Lodge 60 with Wintergreen Advantage
    From $227 per night (USD)

    Expedia

    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 $227 per night (USD)

    Expedia

    Details
  • Three Ridges 74 with Wintergreen Advantage
    From $274 per night (USD)

    VRBO

    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 $274 per night (USD)

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    Details
  • Three Ridges 90 with Wintergreen Advantage
    From $279 per night (USD)

    Expedia

    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 $279 per night (USD)

    Expedia

    Details
  • Highlands 48 with Wintergreen Advantage
    From $397 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 $397 per night (USD)

    VRBO

    Details
  • Cozy Cabin on Cub Creek: Near Wintergreen & AT
    From $235 per night (USD)

    Expedia

    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 $235 per night (USD)

    Expedia

    Details
  • Retreat @ 3 Ridges / 2min->Slopes  / Walk to Dining
    From $282 per night (USD)

    VRBO

    Retreat @ 3 Ridges / 2min->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 $282 per night (USD)

    VRBO

    Details
  • Upscale Wintergreen Getaway.  Golf View Deck, Pool, and Modern Comforts
    From $213 per night (USD)

    Expedia

    Upscale Wintergreen Getaway. Golf View Deck, Pool, and Modern Comforts

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your elegant home away from home at Wintergreen Resort. This 2-bedroom, 2-bathroom condo offers a serene and ...

    From $213 per night (USD)

    Expedia

    Details
  • Art & Soul: Stairless Entry/Living + Sauna/Hot Tub
    From $675 per night (USD)

    VRBO

    Art & Soul: Stairless Entry/Living + Sauna/Hot Tub

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Art & Soul, a newly renovated and stairless entry home in the picturesque mountains of Wintergreen, Virginia. ...

    From $675 per night (USD)

    VRBO

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

    Art & Soul Guest House: Mtn Views + Hot Tub

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    Click For Pricing

    Expedia

    Details
  • Ridge Retreat @ Wintergreen!
    From $549 per night (USD)

    VRBO

    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 $549 per night (USD)

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    Details
  • Blue Rivers Cottage and Loft
    From $449 per night (USD)

    Expedia

    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 $449 per night (USD)

    Expedia

    Details
  • Sycamore Shade: 151 House, HOT TUB, Mountain Views
    From $317 per night (USD)

    VRBO

    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 $317 per night (USD)

    VRBO

    Details
  • Blue Rivers Cottage with Mountain Views
    From $295 per night (USD)

    Expedia

    Blue Rivers Cottage with Mountain Views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

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

    From $295 per night (USD)

    Expedia

    Details
  • Blue Rivers Loft on the Brew Ridge Trail
    From $148 per night (USD)

    VRBO

    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 $148 per night (USD)

    VRBO

    Details
  • Tanners Ridge 14 with Wintergreen Advantage
    From $366 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 $366 per night (USD)

    Expedia

    Details
  • Gumtree 5 with Wintergreen Advantage
    From $486 per night (USD)

    VRBO

    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 $486 per night (USD)

    VRBO

    Details
  • Afton Awaits: Pool & Hot Tub/Central to Wineries
    From $561 per night (USD)

    Expedia

    Afton Awaits: Pool & Hot Tub/Central to Wineries

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $561 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)

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    Details
  • Mountain View Vista: Resort Condo w/ Views
    From $234 per night (USD)

    VRBO

    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 $234 per night (USD)

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  • 6-bedroom house in Nellysford with WiFi AC Skiing Tubing and Golf
    From $413 per night (USD)

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

    Bedrooms:
    3
    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 $413 per night (USD)

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  • Mid-Century Mountain Cabin w/ Hot Tub + Arcade
    From $593 per night (USD)

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    Mid-Century Mountain Cabin w/ Hot Tub + Arcade

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    The perfect blend of mid-century style and family-friendly fun—here’s why guests love our Wintergreen retreat: Top 5 H ...

    From $593 per night (USD)

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  • Red White & WTG: Game Room + Hot Tub
    From $789 per night (USD)

    Expedia

    Red White & WTG: Game Room + Hot Tub

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    16

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

    From $789 per night (USD)

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  • Spacious 5 bedroom modern home with mountain views galore.  Sauna + EV charger.
    From $655 per night (USD)

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    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 $655 per night (USD)

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  • Family Friendly Log Cabin Nestled in Blue Ridge Foothills
    From $174 per night (USD)

    Expedia

    Family Friendly Log Cabin Nestled in Blue Ridge Foothills

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Down a lazy paved road, tucked into the woods on almost 5 acres, Cabin Clover is your perfect home base for exploring an ...

    From $174 per night (USD)

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

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    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)

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

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    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)

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

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    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)

    Expedia

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

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    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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  • Blue Ridge Beech Cabin
    From $283 per night (USD)

    VRBO

    Blue Ridge Beech Cabin

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Summary: Escape to Blue Ridge Beech Cabin. A Cozy Mountain Retreat! Nestled on 13 private acres at the edge of George Wa ...

    From $283 per night (USD)

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

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

    VRBO

    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)

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

    VRBO

    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)

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    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)

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

    VRBO

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

    Expedia

    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)

    VRBO

    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)

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

    Expedia

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

    Expedia

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

    VRBO

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

    Expedia

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

    VRBO

    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 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)

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  • 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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  • 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)

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  • 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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  • 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)

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

    VRBO

    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)

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

    Expedia

    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