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Results: 681 Rentals

  • Northridge 09 with Wintergreen Advantage
    From $596 per night (USD)

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    Northridge 09 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Northridge Spacious Mountain Getaway Make yourself at home in this spacious 3-bedroom, 3-bath condo in Northridge at Wi ...

    From $596 per night (USD)

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  • Overlook 04 with Wintergreen Advantage
    From $507 per night (USD)

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    Overlook 04 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Overlook Mountain Retreat Enjoy a peaceful mountain escape in this 2-bedroom, 2-bath condo in Overlook at Wintergreen R ...

    From $507 per night (USD)

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  • Mountain Inn Lodge 79 with Wintergreen Advantage
    From $297 per night (USD)

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    Mountain Inn Lodge 79 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn King Bed Loft Escape Make the most of your Wintergreen getaway in this inviting loft-style guest room at t ...

    From $297 per night (USD)

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  • Mountain Inn Lodge 63 with Wintergreen Advantage
    From $297 per night (USD)

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    Mountain Inn Lodge 63 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Pet-Friendly King Loft Enjoy a relaxing mountain getaway in this inviting loft-style guest room at the Mou ...

    From $297 per night (USD)

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  • Shenandoah Ridge 09 with Wintergreen Advantage
    From $744 per night (USD)

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    Shenandoah Ridge 09 with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Shenandoah Ridge Spacious Mountain Escape Enjoy a spacious mountain escape in this 4-bedroom, 4-bath condo at Shenandoa ...

    From $744 per night (USD)

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  • Mountain Inn Lodge 52 with Wintergreen Advantage
    From $297 per night (USD)

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    Mountain Inn Lodge 52 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Cozy Loft Retreat Enjoy a charming mountain getaway in this cozy loft-style guest room at the Mountain Inn ...

    From $297 per night (USD)

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  • Overlook 48 with Wintergreen Advantage
    From $829 per night (USD)

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    Overlook 48 with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Overlook Spacious Mountain Retreat Enjoy a spacious mountain escape in this inviting 4-bedroom, 4-bath condo at Overloo ...

    From $829 per night (USD)

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  • Cliffs 26 with Wintergreen Advantage
    From $507 per night (USD)

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    Cliffs 26 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Cliffs Mountain Getaway Relax and enjoy the mountain setting in this 2-bedroom, 2-bath condo in Cliffs, located in Wint ...

    From $507 per night (USD)

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  • Overlook 05 with Wintergreen Advantage
    From $507 per night (USD)

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    Overlook 05 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Overlook Cozy Mountain Escape Escape to the mountains in this 2-bedroom, 2-bath condo in Overlook at Wintergreen Resort ...

    From $507 per night (USD)

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  • Highlands 05 with Wintergreen Advantage
    From $504 per night (USD)

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    Highlands 05 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Highlands Mountain Escape Escape to the mountains in this 2-bedroom, 2-bath condo in Highlands at Wintergreen Resort, n ...

    From $504 per night (USD)

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  • Mountain Inn Lodge 78 with Wintergreen Advantage
    From $297 per night (USD)

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    Mountain Inn Lodge 78 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn King Bed Loft Retreat Settle into a peaceful mountain escape in this cozy loft-style guest room at the Mou ...

    From $297 per night (USD)

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  • Mountain Inn Lodge 62 with Wintergreen Advantage
    From $297 per night (USD)

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    Mountain Inn Lodge 62 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Two-Double Loft Escape Plan a relaxing Wintergreen getaway in this charming loft-style guest room at the M ...

    From $297 per night (USD)

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  • Mountain Inn Lodge 61 with Wintergreen Advantage
    From $297 per night (USD)

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    Mountain Inn Lodge 61 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Two-Queen Loft Retreat Make your next Wintergreen getaway comfortable and convenient in this loft-style gu ...

    From $297 per night (USD)

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  • Trillium Place 01 with Wintergreen Advantage
    From $744 per night (USD)

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    Trillium Place 01 with Wintergreen Advantage

    Bedrooms:
    0
    Bathrooms:
    4
    Sleeps:
    8

    Trillium Spacious Mountain Retreat Escape to the mountains in this spacious 4-bedroom, 3-bath condo at Trillium, locate ...

    From $744 per night (USD)

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    Details
  • Stoneridge 69 with Wintergreen Advantage
    From $604 per night (USD)

    VRBO

    Stoneridge 69 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Stoneridge Pet-Friendly Mountain Retreat Enjoy a memorable mountain getaway in this spacious 3-bedroom, 3-bath condo at ...

    From $604 per night (USD)

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  • Shenandoah Ridge 16 with Wintergreen Advantage
    From $744 per night (USD)

    Expedia

    Shenandoah Ridge 16 with Wintergreen Advantage

    Bedrooms:
    0
    Bathrooms:
    4
    Sleeps:
    8

    Shenandoah Ridge Relaxing Mountain Retreat Experience a relaxing mountain getaway in this spacious 4-bedroom, 4-bath co ...

    From $744 per night (USD)

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    Details
  • Mountain Inn Lodge 58 with Wintergreen Advantage
    From $297 per night (USD)

    VRBO

    Mountain Inn Lodge 58 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn King Bed Loft Getaway Escape to the mountains in this comfortable loft-style guest room at the Mountain In ...

    From $297 per night (USD)

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  • Fairway Woods 36 with Wintergreen Advantage
    From $550 per night (USD)

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    Fairway Woods 36 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Fairway Woods Cozy Mountain Escape Unwind in the peaceful mountain setting of this 3-bedroom, 2-bath condo in Fairway W ...

    From $550 per night (USD)

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    Details
  • Shenandoah Ridge 13 with Wintergreen Advantage
    From $870 per night (USD)

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    Shenandoah Ridge 13 with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Shenandoah Ridge Spacious Mountain Escape Make the most of your Wintergreen getaway in this spacious 5-bedroom, 4-bath ...

    From $870 per night (USD)

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  • Mountain Inn Lodge 55 with Wintergreen Advantage
    From $297 per night (USD)

    Expedia

    Mountain Inn Lodge 55 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Double-Bed Loft Retreat Enjoy a relaxing stay in this inviting loft-style guest room at the Mountain Inn, ...

    From $297 per night (USD)

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    Details
  • Stonewall Court 21 with Wintergreen Advantage
    From $870 per night (USD)

    VRBO

    Stonewall Court 21 with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Stonewall Court Five-Bedroom Mountain Escape Settle into a spacious mountain retreat in this 5-bedroom, 4½-bath condo a ...

    From $870 per night (USD)

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  • Timbers Studio 08 with Wintergreen Advantage
    From $270 per night (USD)

    Expedia

    Timbers Studio 08 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Hotel-Style Escape Enjoy a comfortable mountain getaway in this inviting hotel-style guest room at the ...

    From $270 per night (USD)

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    Details
  • Timbers Studio 05 with Wintergreen Advantage
    From $313 per night (USD)

    VRBO

    Timbers Studio 05 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers Pet-Friendly King Retreat Enjoy a comfortable hotel-style guest room in the Timbers complex, conveniently locat ...

    From $313 per night (USD)

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    Details
  • Mountain Inn Studio 96 with Wintergreen Advantage
    From $270 per night (USD)

    Expedia

    Mountain Inn Studio 96 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Main-Floor King Getaway Settle into a welcoming hotel-style guest room on the main floor of the Mountain I ...

    From $270 per night (USD)

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    Details
  • Laurelwood 44 with Wintergreen Advantage
    From $339 per night (USD)

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    Laurelwood 44 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Laurelwood Mountain Escape Escape to the mountains in this 1-bedroom, 1-bath condo in Laurelwood at Wintergreen Resort, ...

    From $339 per night (USD)

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  • Mountain Inn Studio 97 with Wintergreen Advantage
    From $270 per night (USD)

    Expedia

    Mountain Inn Studio 97 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Pet-Friendly King Retreat Enjoy a relaxing mountain getaway in this charming hotel-style guest room on the ...

    From $270 per night (USD)

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    Details
  • Timbers Studio 07 with Wintergreen Advantage
    From $313 per night (USD)

    VRBO

    Timbers Studio 07 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Hotel-Style Retreat Settle into a welcoming hotel-style guest room in the Timbers complex, convenientl ...

    From $313 per night (USD)

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    Details
  • Highlands 37 with Wintergreen Advantage
    From $360 per night (USD)

    Expedia

    Highlands 37 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Highlands Mountain Retreat Settle into a cozy 1-bedroom, 2-bath condo in Highlands, tucked away in Wintergreen's scenic ...

    From $360 per night (USD)

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    Details
  • Highridge Court 24 with Wintergreen Advantage
    From $360 per night (USD)

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    Highridge Court 24 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Highridge Court Mountain Escape Enjoy a cozy retreat in this 1-bedroom, 2-bath condo in Highridge Court, nestled in Win ...

    From $360 per night (USD)

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  • Laurelwood 84 with Wintergreen Advantage
    From $339 per night (USD)

    Expedia

    Laurelwood 84 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Laurelwood Mountain Getaway Enjoy a cozy retreat in this 1-bedroom, 1-bath condo in Laurelwood at Wintergreen Resort, i ...

    From $339 per night (USD)

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    Details
  • Cliffs 21 with Wintergreen Advantage
    From $360 per night (USD)

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    Cliffs 21 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Cliffs Mountain RetreatCliffs Mountain Retreat Escape to the mountains in this 1-bedroom, 1-bath condo in Cliffs, locat ...

    From $360 per night (USD)

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  • Timbers Studio 06 with Wintergreen Advantage
    From $267 per night (USD)

    Expedia

    Timbers Studio 06 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Hotel-Style Retreat Settle into a cozy hotel-style guest room in the Timbers buildings, conveniently l ...

    From $267 per night (USD)

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    Details
  • Three Ridges 91 with Wintergreen Advantage
    From $465 per night (USD)

    VRBO

    Three Ridges 91 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Three Ridges Cozy Mountain Retreat Make yourself at home in this 2-bedroom, 2-bath condo in the Three Ridges community ...

    From $465 per night (USD)

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  • Nancy's Edelweiss with Wintergreen Advantage
    From $843 per night (USD)

    Expedia

    Nancy's Edelweiss with Wintergreen Advantage

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    This lovely 6-bedroom home is located on a quiet cul-de-sac and only minutes away from the Mountain Inn & main ski area. ...

    From $843 per night (USD)

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  • Chestnut Springs with Wintergreen Advantage
    From $747 per night (USD)

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    Chestnut Springs with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    This beautiful five bedroom home is conveniently located less than one mile from the Devil’s Knob Golf and Tennis Center ...

    From $747 per night (USD)

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  • Bull City Bungalow with Wintergreen Advantage
    From $643 per night (USD)

    Expedia

    Bull City Bungalow with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to our Bull City Bungalow! Bull City Bungalow is a fully renovated and tastefully decorated 4 bedroom, 3 ½ bath ...

    From $643 per night (USD)

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  • Bear Necessities with Wintergreen Advantage
    From $510 per night (USD)

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    Bear Necessities with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Start your adventure and step into Bear Necessities. A picturesque three-bedroom home in the rolling landscape of Winter ...

    From $510 per night (USD)

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  • Blackrock Vista with Wintergreen Advantage
    From $643 per night (USD)

    Expedia

    Blackrock Vista with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

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

    From $643 per night (USD)

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  • Timbers Studio 43 with Wintergreen Advantage
    From $313 per night (USD)

    VRBO

    Timbers Studio 43 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Hotel-Style Retreat Relax in a welcoming hotel-style guest room at the Timbers complex, ideally locate ...

    From $313 per night (USD)

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  • Timbers Studio 14 with Wintergreen Advantage
    From $270 per night (USD)

    Expedia

    Timbers Studio 14 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers Queen Bed Hotel-Style Retreat Make yourself comfortable in this inviting hotel-style guest room at the Timbers ...

    From $270 per night (USD)

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  • Whispering Elm with Wintergreen Advantage
    From $642 per night (USD)

    VRBO

    Whispering Elm with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Whispering Elm is located at the top of the mountain in close proximity to fabulous hiking, skiing, the Devil’s Knob Gol ...

    From $642 per night (USD)

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  • Timbers Studio 18 with Wintergreen Advantage
    From $270 per night (USD)

    Expedia

    Timbers Studio 18 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Hotel-Style Getaway Settle into a welcoming hotel-style guest room at the Timbers complex, ideally loc ...

    From $270 per night (USD)

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    Details
  • Serendipity with Wintergreen Advantage
    From $746 per night (USD)

    VRBO

    Serendipity with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    With only 2 steps to access entry to the house, it is easily accessible for your convenience. A beautiful, large deck is ...

    From $746 per night (USD)

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  • Timbers Studio 13 with Wintergreen Advantage
    From $313 per night (USD)

    Expedia

    Timbers Studio 13 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    "Timbers King Bed Mountain Retreat Make yourself comfortable in this inviting hotel-style guest room at the Timbers com ...

    From $313 per night (USD)

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    Details
  • Timbers Studio 38 with Wintergreen Advantage
    From $267 per night (USD)

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    Timbers Studio 38 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers Pet-Friendly King Retreat Escape to a welcoming hotel-style guest room at the Timbers complex, ideally situated ...

    From $267 per night (USD)

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  • Secluded 20+ Acre Retreat Near Brew & Wine Trails
    From $351 per night (USD)

    Expedia

    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 $351 per night (USD)

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    Details
  • New Blue RIdge Mountains Montebello, Virginia with stary stary skies
    From $211 per night (USD)

    VRBO

    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 $211 per night (USD)

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  • Mountain Mindset: Pup Friendly + Trail
    From $787 per night (USD)

    Expedia

    Mountain Mindset: Pup Friendly + Trail

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Downstairs Living Room: Smart TV, 2 couches, accent chairs (comfortable seating for 7-8). Sitting Room: 4 lounge chair ...

    From $787 per night (USD)

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    Details
  • Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking
    From $227 per night (USD)

    VRBO

    Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Soak in the spectacular views of the Blue Ridge Mountains from the top of Wintergreen Resort. High ceilings and open lay ...

    From $227 per night (USD)

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    Details
  • Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
    From $381 per night (USD)

    Expedia

    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 $381 per night (USD)

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    Details
  • Romantic or Family Vacay w/ Stunning Mtn Views & Hot Tub near Crabtree Falls
    From $390 per night (USD)

    VRBO

    Romantic or Family Vacay w/ Stunning Mtn Views & Hot Tub 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 $390 per night (USD)

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    Details
  • Amazing Views / Hot Tub / 15 mins to Wineries / 3200 sq ft
    From $457 per night (USD)

    Expedia

    Amazing Views / Hot Tub / 15 mins to Wineries / 3200 sq ft

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Welcome to Adrian's Den: a mountaintop hideaway perfect for groups, family reunions, and wedding parties. ★3,200 sq ft ...

    From $457 per night (USD)

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    Details
  • Mountain View Meadow Cottage - Blue Ridge Mountains and Virginia wine country
    From $227 per night (USD)

    VRBO

    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 $227 per night (USD)

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    Details
  • Gum Tree 5 with Wintergreen Advantage
    From $604 per night (USD)

    Expedia

    Gum Tree 5 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Spacious Three-Bedroom Mountain Escape Enjoy a spacious mountain getaway in this apartment-style condominium, featuring ...

    From $604 per night (USD)

    Expedia

    Details
  • \Fall\ in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
    From $312 per night (USD)

    VRBO

    \"Fall\" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & 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 $312 per night (USD)

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    Details
  • Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
    From $328 per night (USD)

    Expedia

    Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy a cozy mountain getaway at this 2BR, 2BA Wintergreen condo, ideally located for ski season and year-round resort a ...

    From $328 per night (USD)

    Expedia

    Details
  • Art & Soul: Sauna/Hot Tub & EV Charger/Hammocks
    From $737 per night (USD)

    VRBO

    Art & Soul: Sauna/Hot Tub & EV Charger/Hammocks

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Living Room: Spacious and inviting with large windows, cozy seating area with a fireplace, coffee table and bookshelf fi ...

    From $737 per night (USD)

    VRBO

    Details
  • Ridge Retreat @ Wintergreen!
    From $554 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 $554 per night (USD)

    Expedia

    Details
  • Blue Rivers Cottage and Loft
    From $513 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 $513 per night (USD)

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    Details
  • Sycamore Shade: 151 House, HOT TUB, Mountain Views
    From $353 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 $353 per night (USD)

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    Details
  • Blue Rivers Cottage with Mountain Views
    From $353 per night (USD)

    VRBO

    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 $353 per night (USD)

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    Details
  • Blue Rivers Loft on the Brew Ridge Trail
    From $166 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 $166 per night (USD)

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    Details
  • Modern 5 bedroom retreat w/ mountain views.  Sauna + Wood fired pizza oven!
    From $864 per night (USD)

    VRBO

    Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

    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 $864 per night (USD)

    VRBO

    Details
  • Afton Awaits: Pool, Mountain View
    From $667 per night (USD)

    Expedia

    Afton Awaits: Pool, Mountain View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Living Room: Spacious and inviting with cozy seating area with a fireplace, coffee table two couches and a smart TV. Di ...

    From $667 per night (USD)

    Expedia

    Details
  • Serene haven \The Nest\ in Wintergreen, close to activities and restaurants.
    From $260 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 $260 per night (USD)

    VRBO

    Details
  • Mountain View Vista: Resort Condo w/ Views
    From $344 per night (USD)

    Expedia

    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 $344 per night (USD)

    Expedia

    Details
  • 6-bedroom house in Nellysford with WiFi AC Skiing Tubing and Golf
    From $821 per night (USD)

    VRBO

    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 $821 per night (USD)

    VRBO

    Details
  • Mid‑Century Retreat • Near Breweries • Sleeps 12
    From $359 per night (USD)

    Expedia

    Mid‑Century Retreat • Near Breweries • Sleeps 12

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Stay minutes from Wintergreen and come home to a place built for group fun — hot tub evenings, a game room for the kids, ...

    From $359 per night (USD)

    Expedia

    Details
  • Red White & WTG: Hot Tub, 5 Bedrooms!
    From $925 per night (USD)

    VRBO

    Red White & WTG: Hot Tub, 5 Bedrooms!

    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 $925 per night (USD)

    VRBO

    Details
  • Laurelwood 95 with Wintergreen Advantage
    From $465 per night (USD)

    Expedia

    Laurelwood 95 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Laurelwood Easy-Access Mountain Retreat Enjoy a relaxing mountain escape in this comfortable 2-bedroom, 2-bath retreat ...

    From $465 per night (USD)

    Expedia

    Details
  • Diamond Hill Studio 09 with Wintergreen Advantage
    From $313 per night (USD)

    VRBO

    Diamond Hill Studio 09 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Diamond Hill Pet-Friendly King Retreat Escape to a cozy mountain getaway in this hotel-style guest room at the Diamond ...

    From $313 per night (USD)

    VRBO

    Details
  • Timbers Studio 44 with Wintergreen Advantage
    From $270 per night (USD)

    Expedia

    Timbers Studio 44 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Hotel-Style Retreat Settle into a comfortable hotel-style guest room at the Timbers complex, convenien ...

    From $270 per night (USD)

    Expedia

    Details
  • Mountain Inn Studio 91 with Wintergreen Advantage
    From $270 per night (USD)

    VRBO

    Mountain Inn Studio 91 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Main-Floor King Retreat Enjoy a comfortable mountain getaway in this charming hotel-style guest room at th ...

    From $270 per night (USD)

    VRBO

    Details
  • Timbers Studio 15 with Wintergreen Advantage
    From $313 per night (USD)

    Expedia

    Timbers Studio 15 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Mountain Retreat Make yourself comfortable in this inviting hotel-style guest room at the Timbers comp ...

    From $313 per night (USD)

    Expedia

    Details
  • Timbers Studio 45 with Wintergreen Advantage
    From $313 per night (USD)

    VRBO

    Timbers Studio 45 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Mountain Escape Enjoy a comfortable hotel-style guest room at the Timbers complex, conveniently positi ...

    From $313 per night (USD)

    VRBO

    Details
  • The Osprey with Wintergreen Advantage
    From $504 per night (USD)

    Expedia

    The Osprey with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Come enjoy the freedom and tranquility of The Osprey perched among the trees and rock out cropping of Wintergreen Mounta ...

    From $504 per night (USD)

    Expedia

    Details
  • Laurelwood 24 with Wintergreen Advantage
    From $465 per night (USD)

    VRBO

    Laurelwood 24 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Laurelwood Cozy Mountain Escape Enjoy a comfortable mountain getaway in Laurelwood at Wintergreen Resort, ideally locat ...

    From $465 per night (USD)

    VRBO

    Details
  • Timbers Studio 47 with Wintergreen Advantage
    From $313 per night (USD)

    Expedia

    Timbers Studio 47 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Hotel-Style Getaway Settle into a cozy hotel-style guest room at the Timbers complex, ideally situated ...

    From $313 per night (USD)

    Expedia

    Details
  • Cabin Blue Ridge with Wintergreen Advantage
    From $503 per night (USD)

    VRBO

    Cabin Blue Ridge with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This new, modern three-bedroom home is tucked away in a quiet location of the resort property, yet has easy, quick acces ...

    From $503 per night (USD)

    VRBO

    Details
  • Timbers Lodge 39 with Wintergreen Advantage
    From $340 per night (USD)

    Expedia

    Timbers Lodge 39 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $340 per night (USD)

    Expedia

    Details
  • Timbers Lodge 23 with Wintergreen Advantage
    From $354 per night (USD)

    VRBO

    Timbers Lodge 23 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers Pet-Friendly King Loft Bring your pup along for a memorable mountain getaway in this cozy loft-style guest room ...

    From $354 per night (USD)

    VRBO

    Details
  • Timbers Lodge 56 with Wintergreen Advantage
    From $297 per night (USD)

    Expedia

    Timbers Lodge 56 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers Queen Bed Loft Retreat Settle into a comfortable mountain getaway in this inviting loft-style guest room at the ...

    From $297 per night (USD)

    Expedia

    Details
  • Timbers Lodge 54 with Wintergreen Advantage
    From $297 per night (USD)

    VRBO

    Timbers Lodge 54 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Loft Escape Discover a comfortable mountain retreat in this loft-style guest room at the Timbers compl ...

    From $297 per night (USD)

    VRBO

    Details
  • Timbers Lodge 58 with Wintergreen Advantage
    From $294 per night (USD)

    Expedia

    Timbers Lodge 58 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Loft Getaway Make the most of your Wintergreen vacation in this welcoming loft-style guest room at the ...

    From $294 per night (USD)

    Expedia

    Details
  • Charming Farmhouse across from Devils Backbone Brewery.
    From $423 per night (USD)

    VRBO

    Charming Farmhouse across from Devils Backbone Brewery.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The Beech Grove Farmhouse is an early century farmhouse situated in the foothills of the Blue Ridge mountains, has a spr ...

    From $423 per night (USD)

    VRBO

    Details
  • Timbers Studio 46 with Wintergreen Advantage
    From $270 per night (USD)

    Expedia

    Timbers Studio 46 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Hotel-Style Getaway Relax in a cozy hotel-style guest room at the Timbers complex, ideally located nea ...

    From $270 per night (USD)

    Expedia

    Details
  • Blue Ridge Retreat with Wintergreen Advantage
    From $2547 per night (USD)

    VRBO

    Blue Ridge Retreat with Wintergreen Advantage

    Bedrooms:
    10
    Bathrooms:
    10
    Sleeps:
    20

    This majestic ten-bedroom, four level home offers all the comforts of a mountain lodge. Named the “Blue Ridge Retreat”, ...

    From $2547 per night (USD)

    VRBO

    Details
  • Wooded Mtn. Retreat with Wintergreen Advantage
    From $844 per night (USD)

    Expedia

    Wooded Mtn. Retreat with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    Wooded Mountain Retreat Wooded Mountain Retreat is nestled in a quiet wooded setting across from the Appalachian Trail a ...

    From $844 per night (USD)

    Expedia

    Details
  • Mountain Inn Studio 94 with Wintergreen Advantage
    From $270 per night (USD)

    VRBO

    Mountain Inn Studio 94 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Main-Floor King Escape Relax in a charming hotel-style guest room on the main floor of the Mountain Inn, i ...

    From $270 per night (USD)

    VRBO

    Details
  • Timbers Lodge 49 with Wintergreen Advantage
    From $340 per night (USD)

    Expedia

    Timbers Lodge 49 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Loft Escape Relax in a welcoming loft-style guest room at the Timbers complex, conveniently located ne ...

    From $340 per night (USD)

    Expedia

    Details
  • Timbers Studio 16 with Wintergreen Advantage
    From $270 per night (USD)

    VRBO

    Timbers Studio 16 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers Pet-Friendly King Retreat Unwind in a cozy hotel-style guest room at the Timbers complex, conveniently located ...

    From $270 per night (USD)

    VRBO

    Details
  • Mountain Inn Studio 95 with Wintergreen Advantage
    From $270 per night (USD)

    Expedia

    Mountain Inn Studio 95 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Main-Floor King Retreat Make yourself at home in this inviting hotel-style guest room on the main floor of ...

    From $270 per night (USD)

    Expedia

    Details
  • Above The Clouds with Wintergreen Advantage
    From $504 per night (USD)

    VRBO

    Above The Clouds with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Experience a stunning mountain retreat and connect with nature at Above The Clouds on Devils Knob Loop. Breathtaking vie ...

    From $504 per night (USD)

    VRBO

    Details
  • Timbers Lodge 50 with Wintergreen Advantage
    From $297 per night (USD)

    Expedia

    Timbers Lodge 50 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Loft Retreat Make yourself comfortable in this inviting loft-style guest room at the Timbers complex, ...

    From $297 per night (USD)

    Expedia

    Details
  • Timbers Lodge 53 with Wintergreen Advantage
    From $340 per night (USD)

    VRBO

    Timbers Lodge 53 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers King Bed Loft Retreat Make yourself at home in this charming loft-style guest room at the Timbers complex, idea ...

    From $340 per night (USD)

    VRBO

    Details
  • Mountaintop Lodge with Wintergreen Advantage
    From $2612 per night (USD)

    Expedia

    Mountaintop Lodge with Wintergreen Advantage

    Bedrooms:
    9
    Bathrooms:
    9
    Sleeps:
    18

    One of Wintergreen’s premier mountain lodges (near the top of the mountain), this beautifully appointed 9 bedroom & 9.5 ...

    From $2612 per night (USD)

    Expedia

    Details
  • Timbers Lodge 57 with Wintergreen Advantage
    From $336 per night (USD)

    VRBO

    Timbers Lodge 57 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers Pet-Friendly King Loft Retreat Bring your pup along for a relaxing Wintergreen getaway in this inviting loft-st ...

    From $336 per night (USD)

    VRBO

    Details
  • Mountain Inn Studio 53 with Wintergreen Advantage
    From $297 per night (USD)

    Expedia

    Mountain Inn Studio 53 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Mountain Inn King & Full Mountain Retreat Settle into a comfortable mountain escape at the Mountain Inn, conveniently s ...

    From $297 per night (USD)

    Expedia

    Details
  • Fairway Woods 44 with Wintergreen Advantage
    From $465 per night (USD)

    VRBO

    Fairway Woods 44 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Fairways Woods Mountain Escape Relax and recharge in this 2-bedroom, 2-bath condo in Fairways Woods, located in Winterg ...

    From $465 per night (USD)

    VRBO

    Details
  • Highlands 42 with Wintergreen Advantage
    From $667 per night (USD)

    Expedia

    Highlands 42 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Highlands Relaxing Mountain Retreat Relax and recharge in this inviting 3-bedroom, 3-bath condo in Highlands at Winterg ...

    From $667 per night (USD)

    Expedia

    Details