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Results: 789 Rentals

  • Cliffs 26 with Wintergreen Advantage
    From $410 per night (USD)

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    Cliffs 26 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
  • Overlook 05 with Wintergreen Advantage
    From $410 per night (USD)

    Expedia

    Overlook 05 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
  • Highlands 05 with Wintergreen Advantage
    From $410 per night (USD)

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    Highlands 05 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
  • Mountain Inn Lodge 78 with Wintergreen Advantage
    From $250 per night (USD)

    Expedia

    Mountain Inn Lodge 78 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 62 with Wintergreen Advantage
    From $250 per night (USD)

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    Mountain Inn Lodge 62 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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  • Mountain Inn Lodge 61 with Wintergreen Advantage
    From $250 per night (USD)

    Expedia

    Mountain Inn Lodge 61 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
  • Trillium Place 01 with Wintergreen Advantage
    From $583 per night (USD)

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    Trillium Place 01 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

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

    From $583 per night (USD)

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  • Stoneridge 69 with Wintergreen Advantage
    From $476 per night (USD)

    Expedia

    Stoneridge 69 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $476 per night (USD)

    Expedia

    Details
  • Shenandoah Ridge 16 with Wintergreen Advantage
    From $528 per night (USD)

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    Shenandoah Ridge 16 with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

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

    From $528 per night (USD)

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    Details
  • Mountain Inn Lodge 58 with Wintergreen Advantage
    From $250 per night (USD)

    Expedia

    Mountain Inn Lodge 58 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
  • Fairway Woods 36 with Wintergreen Advantage
    From $476 per night (USD)

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    Fairway Woods 36 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $476 per night (USD)

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    Details
  • Shenandoah Ridge 13 with Wintergreen Advantage
    From $692 per night (USD)

    Expedia

    Shenandoah Ridge 13 with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

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

    From $692 per night (USD)

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    Details
  • Mountain Inn Lodge 55 with Wintergreen Advantage
    From $250 per night (USD)

    VRBO

    Mountain Inn Lodge 55 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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  • Stonewall Court 21 with Wintergreen Advantage
    From $692 per night (USD)

    Expedia

    Stonewall Court 21 with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

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

    From $692 per night (USD)

    Expedia

    Details
  • Timbers Studio 08 with Wintergreen Advantage
    From $223 per night (USD)

    VRBO

    Timbers Studio 08 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 $223 per night (USD)

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  • Timbers Studio 05 with Wintergreen Advantage
    From $267 per night (USD)

    Expedia

    Timbers Studio 05 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 $267 per night (USD)

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    Details
  • Mountain Inn Studio 96 with Wintergreen Advantage
    From $223 per night (USD)

    VRBO

    Mountain Inn Studio 96 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Hotel style guest room located on the main floor of the Mountain Inn near the Blackrock Village Center and walkable to t ...

    From $223 per night (USD)

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    Details
  • Laurelwood 44 with Wintergreen Advantage
    From $299 per night (USD)

    Expedia

    Laurelwood 44 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)

    Expedia

    Details
  • Mountain Inn Studio 97 with Wintergreen Advantage
    From $224 per night (USD)

    VRBO

    Mountain Inn Studio 97 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Hotel style guest room located on the main floor of the Mountain Inn near the Blackrock Village Center and walkable to t ...

    From $224 per night (USD)

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    Details
  • Timbers Studio 07 with Wintergreen Advantage
    From $267 per night (USD)

    Expedia

    Timbers Studio 07 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 $267 per night (USD)

    Expedia

    Details
  • Highlands 37 with Wintergreen Advantage
    From $299 per night (USD)

    VRBO

    Highlands 37 with Wintergreen Advantage

    Bedrooms:
    2
    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 $299 per night (USD)

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    Details
  • Highridge Court 24 with Wintergreen Advantage
    From $237 per night (USD)

    Expedia

    Highridge Court 24 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 $237 per night (USD)

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    Details
  • Laurelwood 84 with Wintergreen Advantage
    From $299 per night (USD)

    VRBO

    Laurelwood 84 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
  • Cliffs 21 with Wintergreen Advantage
    From $299 per night (USD)

    Expedia

    Cliffs 21 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $299 per night (USD)

    Expedia

    Details
  • Timbers Studio 06 with Wintergreen Advantage
    From $223 per night (USD)

    VRBO

    Timbers Studio 06 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Hotel style guest room located in the Timbers building. One King bed with kitchenette. All accommodations involve stai ...

    From $223 per night (USD)

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    Details
  • Three Ridges 91 with Wintergreen Advantage
    From $309 per night (USD)

    Expedia

    Three Ridges 91 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 $309 per night (USD)

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    Details
  • La Mandala with Wintergreen Advantage
    From $926 per night (USD)

    VRBO

    La Mandala with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    12

    6-Bedroom Home / Sleeps 12 Home Features • 2,913 sq ft • Full kitchen with wood stove with open floor plan into dining a ...

    From $926 per night (USD)

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    Details
  • Nancy's Edelweiss with Wintergreen Advantage
    From $677 per night (USD)

    Expedia

    Nancy's Edelweiss with Wintergreen Advantage

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    12

    6-Bedroom Home / Sleeps 12 Home Features • 3,792 sq ft • Six Bedrooms: One King / One King / Two Doubles / Two Doubles / ...

    From $677 per night (USD)

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  • Chestnut Springs with Wintergreen Advantage
    From $610 per night (USD)

    VRBO

    Chestnut Springs with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    5-Bedroom Home / Sleeps 10 Home Features • 3300 Square Feet • 5 steps from parking lot to front entrance • Gas Fireplace ...

    From $610 per night (USD)

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  • Bull City Bungalow with Wintergreen Advantage
    From $506 per night (USD)

    Expedia

    Bull City Bungalow with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    4-Bedroom Home / Sleeps 8 Home Features: • Four Bedrooms: One King / One King / One Double / One Double • 2660 sq. ft • ...

    From $506 per night (USD)

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    Details
  • Bear Necessities with Wintergreen Advantage
    From $430 per night (USD)

    VRBO

    Bear Necessities with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    3-Bedroom Home / Sleeps 6 Home Features: • 1,196 sq ft • Living Room with Gas Fireplace • Complete Kitchen with Full-si ...

    From $430 per night (USD)

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    Details
  • Blackrock Vista with Wintergreen Advantage
    From $525 per night (USD)

    Expedia

    Blackrock Vista with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    4-Bedroom Home / Sleeps 8 Home Features • 3008 Square Feet • Complete modern kitchen with full-size refrigerator, stove, ...

    From $525 per night (USD)

    Expedia

    Details
  • Timbers Studio 43 with Wintergreen Advantage
    From $267 per night (USD)

    VRBO

    Timbers Studio 43 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 $267 per night (USD)

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    Details
  • The 19th Hole with Wintergreen Advantage
    From $468 per night (USD)

    Expedia

    The 19th Hole with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    3-Bedroom Home / Sleeps 6 Home Features: • Living Room with Wood Fireplace, Dining Area • 2448 sq. ft • Complete Kitchen ...

    From $468 per night (USD)

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  • Whispering Elm with Wintergreen Advantage
    From $536 per night (USD)

    VRBO

    Whispering Elm with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    4-Bedroom Home / Sleeps 8 Home Features • 3,171 sq ft • Full kitchen with open floor plan • Great room with cathedral ce ...

    From $536 per night (USD)

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  • Timbers Studio 18 with Wintergreen Advantage
    From $222 per night (USD)

    Expedia

    Timbers Studio 18 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 $222 per night (USD)

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    Details
  • Fern Hollow with Wintergreen Advantage
    From $771 per night (USD)

    VRBO

    Fern Hollow with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    4-Bedroom Home Home Features • 2,000 sq ft • Multi-level home • Full kitchen with open floor plan of kitchen, dining, an ...

    From $771 per night (USD)

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    Details
  • Serendipity with Wintergreen Advantage
    From $620 per night (USD)

    Expedia

    Serendipity with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    5-Bedroom Home / Sleeps 10 Home Features • 2,560 sq ft • Five Bedrooms: One King / One Queen / One Queen / One Queen / ...

    From $620 per night (USD)

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    Details
  • Timbers Studio 13 with Wintergreen Advantage
    From $270 per night (USD)

    VRBO

    Timbers Studio 13 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 $270 per night (USD)

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    Details
  • Timbers Studio 38 with Wintergreen Advantage
    From $223 per night (USD)

    Expedia

    Timbers Studio 38 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 $223 per night (USD)

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    Details
  • Three Ridges 84 with Wintergreen Advantage
    From $299 per night (USD)

    VRBO

    Three Ridges 84 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
  • Shenandoah Ridge 07 with Wintergreen Advantage
    From $583 per night (USD)

    Expedia

    Shenandoah Ridge 07 with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

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

    From $583 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 68 with Wintergreen Advantage
    From $250 per night (USD)

    VRBO

    Mountain Inn Lodge 68 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
  • Stoneridge 82 with Wintergreen Advantage
    From $476 per night (USD)

    Expedia

    Stoneridge 82 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $476 per night (USD)

    Expedia

    Details
  • Westwood 01 with Wintergreen Advantage
    From $589 per night (USD)

    VRBO

    Westwood 01 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Located in the Westwood condominium complex on Ivy Glen Lane, in the Devils Knob area with close proximity to The Spa, A ...

    From $589 per night (USD)

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    Details
  • Laurelwood 95 with Wintergreen Advantage
    From $314 per night (USD)

    Expedia

    Laurelwood 95 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 $314 per night (USD)

    Expedia

    Details
  • Dragon's Back with Wintergreen Advantage
    From $2073 per night (USD)

    VRBO

    Dragon's Back with Wintergreen Advantage

    Bedrooms:
    9
    Bathrooms:
    9
    Sleeps:
    18

    9-Bedroom Home / Sleeps 18 Home Features • One-of-a-kind 7,600 sq ft two-story home, completely rebuilt in 2022 • Amazin ...

    From $2073 per night (USD)

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    Details
  • Diamond Hill Studio 09 with Wintergreen Advantage
    From $267 per night (USD)

    Expedia

    Diamond Hill Studio 09 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Hotel style guest room located in the Diamond Hill condominium complex, near the Blackrock Village Center and walkable t ...

    From $267 per night (USD)

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    Details
  • A-Frame @ WTG Resort w\/ Hot Tub\n\n
    From $335 per night (USD)

    VRBO

    A-Frame @ WTG Resort w\/ Hot Tub\n\n

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Recently Renovated, Bright, and a Serene place to relax with the family between hikes or time on the slopes! Our A-frame ...

    From $335 per night (USD)

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    Details
  • Romantic Mountain Retreat or Family Vacay w\/ Stunning Views near Crabtree Falls
    From $301 per night (USD)

    Expedia

    Romantic Mountain Retreat or Family Vacay w\/ Stunning Views near Crabtree Falls

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Enjoy a romantic getaway or relax with the whole family on a special family vacation at this peaceful retreat in the mou ...

    From $301 per night (USD)

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    Details
  • Hot Tub \/ Bunk Room \/ 2 Living Rooms \/ King Beds \/ 3,200 sqft
    From $631 per night (USD)

    VRBO

    Hot Tub \/ Bunk Room \/ 2 Living Rooms \/ King Beds \/ 3,200 sqft

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Welcome to Adrian's Den, a cozy mountain retreat nestled in the heart of Wintergreen Resort. Enjoy not only close proxim ...

    From $631 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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  • Mountain View Meadow Cottage - Blue Ridge Mountains and Virginia wine country
    From $239 per night (USD)

    Expedia

    Mountain View Meadow Cottage - Blue Ridge Mountains and Virginia wine country

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Cottage in the heart of the Blue Ridge Mountains and Virginia wine country. Kick back and relax in this calm and stylis ...

    From $239 per night (USD)

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    Details
  • Condo in Wintergreen Resort
    From $149 per night (USD)

    VRBO

    Condo in Wintergreen Resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wintergreen is a beautiful in all four seasons and a must visit any time of year. Families of all ages will love explori ...

    From $149 per night (USD)

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    Details
  • 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
  • Secluded 20+ Acre Retreat Near Brew & Wine Trails
    From $446 per night (USD)

    VRBO

    Secluded 20+ Acre Retreat Near Brew & Wine Trails

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Your Nelson County Retreat Escape to our charming and family-friendly home set on over 20 private, quiet and ...

    From $446 per night (USD)

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    Details
  • New Blue RIdge Mountains Montebello, Virginia with stary stary skies
    From $225 per night (USD)

    Expedia

    New Blue RIdge Mountains Montebello, Virginia with stary stary skies

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    idyllic setting by North Fork of Tye River. Sit on deck or by fire pit. Free wood provided. 100 acre parcel that you ...

    From $225 per night (USD)

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    Details
  • Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
    From $305 per night (USD)

    VRBO

    Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Chestnut House The perfect place for you and your family to rest, unplug, enjoy novice trout fishing, and stargaze ...

    From $305 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
  • Retreat @ 3 Ridges \/ 3min->Slopes  \/ Walk to Dining
    From $303 per night (USD)

    VRBO

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

    Expedia

    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)

    VRBO

    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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  • 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)

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

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    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)

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

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    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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  • 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)

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

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

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    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)

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

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    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)

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

    Expedia

    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)

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

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    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
  • *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)

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  • 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)

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  • 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)

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    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)

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

    Expedia

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

    VRBO

    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)

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

    Expedia

    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
  • 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)

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  • Family Friendly Log Cabin Nestled in Blue Ridge Foothills
    From $214 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 $214 per night (USD)

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    Details
  • Castle Snow with Wintergreen Advantage
    From $525 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 $525 per night (USD)

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  • 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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  • 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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  • Blue Ridge Beech Cabin
    From $282 per night (USD)

    VRBO

    Blue Ridge Beech Cabin

    Bedrooms:
    2
    Bathrooms:
    4
    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 $282 per night (USD)

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

    Expedia

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

    VRBO

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

    Expedia

    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)

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

    VRBO

    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)

    Expedia

    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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    Details
  • Our Mountain Getaway, For Graduation & Easter
    From $1022 per night (USD)

    VRBO

    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)

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  • Cliffs Edge,Hike, Play & Splash into Summer! Camps too!
    From $427 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 $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)

    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 $189 per night (USD)

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

    Expedia

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

    VRBO

    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)

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

    Expedia

    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)

    Expedia

    Details