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Results: 681 Rentals

  • Fairway Woods 34 with Wintergreen Advantage
    From $458 per night (USD)

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    Fairway Woods 34 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Fairways Woods Mountain Escape Unwind in this 2-bedroom, 2-bath condo in Fairways Woods, located in Wintergreen's sceni ...

    From $458 per night (USD)

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    Details
  • Dobie 54 with Wintergreen Advantage
    From $731 per night (USD)

    Expedia

    Dobie 54 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Dobie Mountain Getaway Enjoy the perfect mountain escape in this comfortable 3-bedroom, 3-bath condo at Dobie, convenie ...

    From $731 per night (USD)

    Expedia

    Details
  • Fairway Woods 21 with Wintergreen Advantage
    From $604 per night (USD)

    VRBO

    Fairway Woods 21 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Fairway Woods Mountain Retreat Escape to the mountains in this inviting 3-bedroom, 2-bath condo in Fairway Woods at Win ...

    From $604 per night (USD)

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  • Cliffs 07 with Wintergreen Advantage
    From $501 per night (USD)

    Expedia

    Cliffs 07 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Cliffs Mountain Serenity Escape to the mountain serenity of The Cliffs at Wintergreen Resort in this comfortable 2-bedr ...

    From $501 per night (USD)

    Expedia

    Details
  • Highlands 23 with Wintergreen Advantage
    From $546 per night (USD)

    VRBO

    Highlands 23 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Mountain Getaway at Wintergreen Resort Escape to the mountains in this 2-bedroom, 2-bath condo in the scenic Devils Kno ...

    From $546 per night (USD)

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  • Stoneridge 26 with Wintergreen Advantage
    From $465 per night (USD)

    Expedia

    Stoneridge 26 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Stoneridge Mountain Getaway Escape to the mountains in this 2-bedroom, 2-bath condo in Stoneridge, located in Wintergre ...

    From $465 per night (USD)

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    Details
  • Ledges 71 with Wintergreen Advantage
    From $507 per night (USD)

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    Ledges 71 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Ledges Mountain Retreat Experience the beauty of Wintergreen in this 2-bedroom, 2-bath condo in Ledges, nestled in the ...

    From $507 per night (USD)

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    Details
  • Diamond Hill 49 with Wintergreen Advantage
    From $549 per night (USD)

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    Diamond Hill 49 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Diamond Hill Mountain Escape Relax and recharge in this 2-bedroom, 2-bath condo in Diamond Hill at Wintergreen Resort. ...

    From $549 per night (USD)

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    Details
  • Stoneridge 29 with Wintergreen Advantage
    From $378 per night (USD)

    VRBO

    Stoneridge 29 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Stoneridge Cozy Mountain Retreat Unwind in this 2-bedroom, 2-bath condo in Stoneridge, nestled in Wintergreen's scenic ...

    From $378 per night (USD)

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    Details
  • Vistas 71 with Wintergreen Advantage
    From $360 per night (USD)

    Expedia

    Vistas 71 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Vistas Mountain Getaway Unwind in this 1-bedroom, 2-bath condo in Vistas, nestled in Wintergreen's scenic Devils Knob a ...

    From $360 per night (USD)

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    Details
  • Shenandoah Ridge 02 with Wintergreen Advantage
    From $744 per night (USD)

    VRBO

    Shenandoah Ridge 02 with Wintergreen Advantage

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Shenandoah Ridge Spacious Mountain Retreat Enjoy a spacious mountain getaway in this 4-bedroom, 4-bath condo at Shenand ...

    From $744 per night (USD)

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    Details
  • Highridge Place 43 with Wintergreen Advantage
    From $355 per night (USD)

    Expedia

    Highridge Place 43 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Highridge Place Mountain Retreat Escape to the mountains in this 1-bedroom, 1-bath condo in Highridge Place, nestled in ...

    From $355 per night (USD)

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    Details
  • Stoneridge 42 with Wintergreen Advantage
    From $604 per night (USD)

    VRBO

    Stoneridge 42 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Stoneridge Spacious Mountain Getaway Experience a relaxing Wintergreen getaway in this spacious 3-bedroom, 3-bath condo ...

    From $604 per night (USD)

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    Details
  • Stoneridge 30 with Wintergreen Advantage
    From $604 per night (USD)

    Expedia

    Stoneridge 30 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Stoneridge Spacious Mountain Escape Escape to the beauty of Wintergreen Resort in this spacious 3-bedroom, 3-bath condo ...

    From $604 per night (USD)

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    Details
  • Overlook 45 with Wintergreen Advantage
    From $667 per night (USD)

    VRBO

    Overlook 45 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Overlook Spacious Mountain Retreat Take in the beauty of Wintergreen from this spacious 3-bedroom, 3-bath condo at Over ...

    From $667 per night (USD)

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    Details
  • Laurelwood 73 with Wintergreen Advantage
    From $465 per night (USD)

    Expedia

    Laurelwood 73 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Laurelwood Cozy Mountain Retreat Make yourself at home in this cozy 2-bedroom, 2-bath retreat in Laurelwood at Wintergr ...

    From $465 per night (USD)

    Expedia

    Details
  • Vistas 64 with Wintergreen Advantage
    From $507 per night (USD)

    VRBO

    Vistas 64 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Vistas Cozy Mountain Escape Enjoy a comfortable mountain getaway in this 2-bedroom, 2-bath condo in Vistas at Wintergre ...

    From $507 per night (USD)

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    Details
  • Laurelwood 80 with Wintergreen Advantage
    From $465 per night (USD)

    Expedia

    Laurelwood 80 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Laurelwood Mountain Getaway Relax and enjoy a mountain escape in this 2-bedroom, 2-bath retreat in Laurelwood at Winter ...

    From $465 per night (USD)

    Expedia

    Details
  • Stoneridge Woods 05 with Wintergreen Advantage
    From $458 per night (USD)

    VRBO

    Stoneridge Woods 05 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Stoneridge Woods Mountain Retreat Enjoy a relaxing escape in this 2-bedroom, 2-bath condo in Stoneridge Woods, nestled ...

    From $458 per night (USD)

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

    Expedia

    Overlook 26 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Overlook Mountain Getaway Enjoy a comfortable mountain getaway in this 2-bedroom, 2-bath condo in the Overlook communit ...

    From $507 per night (USD)

    Expedia

    Details
  • Fairway Woods 43 with Wintergreen Advantage
    From $463 per night (USD)

    VRBO

    Fairway Woods 43 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Fairways Woods Mountain Retreat Escape to the mountains in this 2-bedroom, 2-bath condo in Fairways Woods, nestled in W ...

    From $463 per night (USD)

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    Details
  • Highridge Court 19 with Wintergreen Advantage
    From $667 per night (USD)

    Expedia

    Highridge Court 19 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Highridge Court Pet-Friendly Mountain Retreat Enjoy a comfortable mountain getaway in this spacious 3-bedroom, 3-bath c ...

    From $667 per night (USD)

    Expedia

    Details
  • Stoneridge 75 with Wintergreen Advantage
    From $465 per night (USD)

    VRBO

    Stoneridge 75 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Stoneridge Mountain Getaway Enjoy a relaxing escape in this 2-bedroom, 2-bath condo in Stoneridge, nestled in Wintergre ...

    From $465 per night (USD)

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    Details
  • Eagles Court 19 with Wintergreen Advantage
    From $542 per night (USD)

    Expedia

    Eagles Court 19 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Eagles Court Cozy Mountain Retreat Settle into a comfortable 2-bedroom, 1½-bath condo in Eagles Court at Wintergreen Re ...

    From $542 per night (USD)

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    Details
  • Laurelwood 25 with Wintergreen Advantage
    From $465 per night (USD)

    VRBO

    Laurelwood 25 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Laurelwood Cozy Mountain Retreat Settle into a comfortable mountain getaway in this inviting 2-bedroom, 2-bath retreat ...

    From $465 per night (USD)

    VRBO

    Details
  • Laurelwood 43 with Wintergreen Advantage
    From $465 per night (USD)

    Expedia

    Laurelwood 43 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Laurelwood Easy-Access Mountain Escape Enjoy a convenient mountain getaway in this 2-bedroom, 2-bath condo in Laurelwoo ...

    From $465 per night (USD)

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    Details
  • Vistas 82 with Wintergreen Advantage
    From $667 per night (USD)

    VRBO

    Vistas 82 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $667 per night (USD)

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    Details
  • White Oak 46 with Wintergreen Advantage
    From $604 per night (USD)

    Expedia

    White Oak 46 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    White Oak Spacious Mountain Retreat Escape to the mountains in this spacious 3-bedroom, 2-bath condo in the White Oak c ...

    From $604 per night (USD)

    Expedia

    Details
  • Highlands 17 with Wintergreen Advantage
    From $360 per night (USD)

    VRBO

    Highlands 17 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Peaceful Highlands Getaway Escape to the mountains in this 1-bedroom, 1-bath condo in Highlands, located in Wintergreen ...

    From $360 per night (USD)

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    Details
  • Highridge Court 30 with Wintergreen Advantage
    From $359 per night (USD)

    Expedia

    Highridge Court 30 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Highridge Court Cozy Retreat Escape to the mountains in this 1-bedroom, 1-bath condo in Highridge Court, located in Win ...

    From $359 per night (USD)

    Expedia

    Details
  • Dobie 43 with Wintergreen Advantage
    From $549 per night (USD)

    VRBO

    Dobie 43 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Dobie Mountain Retreat Settle into a comfortable 2-bedroom, 2-bath condo in Dobie at Wintergreen Resort, ideally locate ...

    From $549 per night (USD)

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    Details
  • Dobie 04 with Wintergreen Advantage
    From $549 per night (USD)

    Expedia

    Dobie 04 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Dobie Mountain Retreat Make yourself at home in this 2-bedroom, 2-bath condo in Dobie at Wintergreen Resort, convenient ...

    From $549 per night (USD)

    Expedia

    Details
  • Highridge Place 42 with Wintergreen Advantage
    From $507 per night (USD)

    VRBO

    Highridge Place 42 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Highridge Place Cozy Mountain Retreat Settle into a comfortable mountain getaway in this 2-bedroom, 2-bath condo in Hig ...

    From $507 per night (USD)

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    Details
  • White Oak 51 with Wintergreen Advantage
    From $587 per night (USD)

    Expedia

    White Oak 51 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    White Oak Cozy Mountain Retreat Settle into a comfortable mountain getaway in this 3-bedroom, 2-bath condo in the White ...

    From $587 per night (USD)

    Expedia

    Details
  • Three Ridges 59 with Wintergreen Advantage
    From $463 per night (USD)

    VRBO

    Three Ridges 59 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Three Ridges Mountain Getaway Stay close to the action in this 2-bedroom, 2-bath condo in the Three Ridges community at ...

    From $463 per night (USD)

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    Details
  • Cliffs 27 with Wintergreen Advantage
    From $507 per night (USD)

    Expedia

    Cliffs 27 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Cliffs Cozy Mountain Retreat Discover a comfortable escape in this 2-bedroom, 2-bath condo in Cliffs, nestled in Winter ...

    From $507 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 65 with Wintergreen Advantage
    From $297 per night (USD)

    VRBO

    Mountain Inn Lodge 65 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Two-Queen Mountain Retreat Settle into a comfortable mountain escape in this loft-style guest room at the ...

    From $297 per night (USD)

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    Details
  • Overlook 43 with Wintergreen Advantage
    From $507 per night (USD)

    Expedia

    Overlook 43 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Overlook Pet-Friendly Mountain Escape Escape to Wintergreen in this 2-bedroom, 2-bath condo at Overlook, nestled in the ...

    From $507 per night (USD)

    Expedia

    Details
  • Dobie 16 with Wintergreen Advantage
    From $458 per night (USD)

    VRBO

    Dobie 16 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Dobie Mountain Getaway Escape to the mountains in this 2-bedroom, 2-bath condo in Dobie at Wintergreen Resort. Located ...

    From $458 per night (USD)

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    Details
  • Fairway Woods 01 with Wintergreen Advantage
    From $465 per night (USD)

    Expedia

    Fairway Woods 01 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Fairways Woods Mountain Retreat Escape to the mountains in this 2-bedroom, 2-bath condo in Fairways Woods, located in W ...

    From $465 per night (USD)

    Expedia

    Details
  • Stoneridge 43 with Wintergreen Advantage
    From $339 per night (USD)

    VRBO

    Stoneridge 43 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Cozy Devils Knob Retreat at Wintergreen Resort Escape to the mountains in this 1-bedroom, 2-bath condo in Stoneridge, l ...

    From $339 per night (USD)

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    Details
  • Eagles Court 27 with Wintergreen Advantage
    From $549 per night (USD)

    Expedia

    Eagles Court 27 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Eagles Court Mountain Retreat Escape to the mountains in this 2-bedroom, 2-bath condo in Eagles Court at Wintergreen Re ...

    From $549 per night (USD)

    Expedia

    Details
  • Stoneridge 77 with Wintergreen Advantage
    From $334 per night (USD)

    VRBO

    Stoneridge 77 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Cozy Mountain Retreat at Wintergreen Resort Escape to the mountains in this 1-bedroom, 2-bath condo in Stoneridge, nest ...

    From $334 per night (USD)

    VRBO

    Details
  • Overlook 41 with Wintergreen Advantage
    From $507 per night (USD)

    Expedia

    Overlook 41 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Overlook Cozy Mountain Stay Settle into a comfortable mountain getaway in this 2-bedroom, 2-bath condo in the Overlook ...

    From $507 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 76 with Wintergreen Advantage
    From $297 per night (USD)

    VRBO

    Mountain Inn Lodge 76 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn King Bed Loft Escape Enjoy the charm of a mountain getaway in this inviting loft-style guest room at the M ...

    From $297 per night (USD)

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    Details
  • Mountain Inn Lodge 70 with Wintergreen Advantage
    From $297 per night (USD)

    Expedia

    Mountain Inn Lodge 70 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn King Bed Mountain Retreat Settle into a cozy mountain hideaway in this loft-style guest room at the Mounta ...

    From $297 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 64 with Wintergreen Advantage
    From $297 per night (USD)

    VRBO

    Mountain Inn Lodge 64 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Two-Queen Loft Escape Make yourself comfortable in this inviting loft-style guest room at the Mountain Inn ...

    From $297 per night (USD)

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    Details
  • Mountain Inn Lodge 71 with Wintergreen Advantage
    From $297 per night (USD)

    Expedia

    Mountain Inn Lodge 71 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn King Bed Loft Getaway Unwind in a charming loft-style guest room at the Mountain Inn, conveniently situate ...

    From $297 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 82 with Wintergreen Advantage
    From $294 per night (USD)

    VRBO

    Mountain Inn Lodge 82 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Two-Queen Loft Getaway Experience a relaxing stay in this inviting loft-style guest room at the Mountain I ...

    From $294 per night (USD)

    VRBO

    Details
  • Mountain Inn Lodge 59 with Wintergreen Advantage
    From $297 per night (USD)

    Expedia

    Mountain Inn Lodge 59 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Double Bed Loft Getaway Settle into a comfortable mountain retreat in this loft-style guest room at the Mo ...

    From $297 per night (USD)

    Expedia

    Details
  • Mountain Inn Lodge 83 with Wintergreen Advantage
    From $294 per night (USD)

    VRBO

    Mountain Inn Lodge 83 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Two-Queen Loft Retreat Enjoy a comfortable mountain stay in this charming loft-style guest room at the Mou ...

    From $294 per night (USD)

    VRBO

    Details
  • Mountain Inn Lodge 60 with Wintergreen Advantage
    From $297 per night (USD)

    Expedia

    Mountain Inn Lodge 60 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn King Bed Loft Retreat Discover a relaxing mountain escape in this charming loft-style guest room at the Mo ...

    From $297 per night (USD)

    Expedia

    Details
  • Three Ridges 74 with Wintergreen Advantage
    From $339 per night (USD)

    VRBO

    Three Ridges 74 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Three Ridges Cozy Mountain Retreat Settle into a charming 1-bedroom, 1-bath condo in Three Ridges at Wintergreen Resort ...

    From $339 per night (USD)

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    Details
  • Majestic Mtn Cabin w quick hiking & overlook access
    From $462 per night (USD)

    Expedia

    Majestic Mtn Cabin w quick hiking & overlook access

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

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

    From $462 per night (USD)

    Expedia

    Details
  • Walk to Ski Slopes: Wintergreen Resort ‘Treehouse’
    From $307 per night (USD)

    VRBO

    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 $307 per night (USD)

    VRBO

    Details
  • Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.
    Click For Pricing

    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 ...

    Click For Pricing

    Expedia

    Details
  • Unwind at Bear Pause, located right at Wintergreen Resort.
    From $459 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 $459 per night (USD)

    VRBO

    Details
  • Wintergreen 5BR with Hot Tub, Sauna, Firepit
    From $1043 per night (USD)

    Expedia

    Wintergreen 5BR with Hot Tub, Sauna, Firepit

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Welcome to Marigold on the Mountain! Located in the heart of Wintergreen, Marigold features a hot tub and cedar barrel s ...

    From $1043 per night (USD)

    Expedia

    Details
  • Mountain Views, Hot Tub, Impeccable Design
    From $1132 per night (USD)

    VRBO

    Mountain Views, Hot Tub, Impeccable Design

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    Welcome to Chasing Altitudes, a designer-decorated Wintergreen home with fantastic year-round views. The multiple decks ...

    From $1132 per night (USD)

    VRBO

    Details
  • Overlook 180 degree views w/Peloton!
    From $444 per night (USD)

    Expedia

    Overlook 180 degree views w/Peloton!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy some of the best views at Wintergreen from this updated Overlook condo. Take in beautiful sunrises from the privat ...

    From $444 per night (USD)

    Expedia

    Details
  • Altitude Adjustment-It's Pumpkin Spice Time!
    From $240 per night (USD)

    VRBO

    Altitude Adjustment-It's Pumpkin Spice Time!

    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)

    VRBO

    Details
  • Slopes @ Tyro
    From $456 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 $456 per night (USD)

    Expedia

    Details
  • Our Mountain Getaway
    From $674 per night (USD)

    VRBO

    Our Mountain Getaway

    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 $674 per night (USD)

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  • Cliffs Edge-A Contemporary Mountain Home
    From $494 per night (USD)

    Expedia

    Cliffs Edge-A Contemporary Mountain Home

    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 $494 per night (USD)

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  • Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
    From $299 per night (USD)

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    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 $299 per night (USD)

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  • Privacy and Views in Wintergreen
    From $427 per night (USD)

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    Privacy and Views in Wintergreen

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    Welcome to our cozy Wintergreen home, located on one of the most private lots in the area. You'll truly feel at peace wi ...

    From $427 per night (USD)

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  • Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
    From $973 per night (USD)

    VRBO

    Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds

    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 $973 per night (USD)

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  • Wintergreen Mountain Top Escape: Steps to Golf, Hiking & High-Country Views
    From $392 per night (USD)

    Expedia

    Wintergreen Mountain Top Escape: Steps to Golf, Hiking & High-Country Views

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    • Things to know (we want you to relax, not waste your time!) • 4 bedrooms (sleeps 10) • 3 Full baths • No pets • Yes, v ...

    From $392 per night (USD)

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  • Highridge 06 with Wintergreen Advantage
    From $507 per night (USD)

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    Highridge 06 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Highridge Mountain Getaway Enjoy a relaxing mountain escape in this 2-bedroom, 2-bath condo in the Highridge community ...

    From $507 per night (USD)

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  • Wintergreen Luxury, Breathtaking Views
    From $799 per night (USD)

    Expedia

    Wintergreen Luxury, Breathtaking Views

    Bedrooms:
    4
    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 $799 per night (USD)

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  • Timbers 11 With Wintergreen Advantage
    From $354 per night (USD)

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    Timbers 11 With Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Timbers One-Bedroom King Condo Enjoy a relaxing mountain retreat in this inviting one-bedroom condo at the Timbers, con ...

    From $354 per night (USD)

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  • Three Ridges 05 With Wintergreen Advantage
    From $465 per night (USD)

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    Three Ridges 05 With Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Three Ridges Ski-Access Retreat Enjoy a comfortable mountain getaway in this 2-bedroom, 2-bath condo in the Three Ridge ...

    From $465 per night (USD)

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  • Lofty Pursuits: Spectacular View + EV Charger
    From $420 per night (USD)

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    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 $420 per night (USD)

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  • Three Little Bears: Walk to Ski & Swim
    From $310 per night (USD)

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    Three Little Bears: Walk to Ski & Swim

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FIRST FLOOR: LIVING ROOM - NEW sectional sofa, smart TV, wood-burning fireplace (firewood provided), board gams and ki ...

    From $310 per night (USD)

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  • New Build! Log Cabin with Hot Tub in Wintergreen
    From $467 per night (USD)

    VRBO

    New Build! Log Cabin with Hot Tub in Wintergreen

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    15

    Welcome to Loggin' Off, a log cabin built in 2024 in the heart of Wintergreen. This 6 bedroom home sleeps 15 and feature ...

    From $467 per night (USD)

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  • Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard
    From $343 per night (USD)

    Expedia

    Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Escape to this cozy four-season mountain retreat tucked away on a private wooded lot in the heart of Wintergreen Resort. ...

    From $343 per night (USD)

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  • Mntn View Hot Tub Foosball Fireplace Multi-Deck
    From $520 per night (USD)

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    Mntn View Hot Tub Foosball Fireplace Multi-Deck

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    4min drive to Wintergreen skiing. Adventure and relaxation await at this mountain top Wintergreen Resort home! With 4 be ...

    From $520 per night (USD)

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  • Dragon's Back, 9BR 10BA in Wintergreen
    From $2082 per night (USD)

    Expedia

    Dragon's Back, 9BR 10BA in Wintergreen

    Bedrooms:
    10
    Bathrooms:
    9
    Sleeps:
    18

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

    From $2082 per night (USD)

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  • Pet-Friendly King Suite w/ Desk & Smart Entry
    From $168 per night (USD)

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    Pet-Friendly King Suite w/ Desk & Smart Entry

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Experience laid-back comfort in this inviting 1-bedroom suite featuring a king bed, queen sleeper sofa, and an in-suite ...

    From $168 per night (USD)

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  • Wintergreen Condo w/ Pool: Near Hike & Market!
    From $216 per night (USD)

    Expedia

    Wintergreen Condo w/ Pool: Near Hike & Market!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Walk to Wintergreen Conference Center | Near Hiking Trails | Community Pool Access Experience the best of the mountains ...

    From $216 per night (USD)

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  • Three Ridges 27 With Wintergreen Advantage
    From $604 per night (USD)

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    Three Ridges 27 With Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Three Ridges Charming Mountain Escape Make yourself at home in this charming 3-bedroom, 2-bath condo at Three Ridges, i ...

    From $604 per night (USD)

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  • Three Ridges 64 With Wintergreen Advantage
    From $339 per night (USD)

    Expedia

    Three Ridges 64 With Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Three Ridges Mountain Getaway Escape to the mountains in this 1-bedroom, 1-bath condo in Three Ridges at Wintergreen Re ...

    From $339 per night (USD)

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  • Treetop Mountain Escape - Fireplace, Views & Pool
    From $225 per night (USD)

    VRBO

    Treetop Mountain Escape - Fireplace, Views & Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wake up above the treetops in this beautifully updated top-floor condo at Wintergreen Resort — Virginia’s premier four-s ...

    From $225 per night (USD)

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  • Antlers Aweigh with Wintergreen Advantage
    From $643 per night (USD)

    Expedia

    Antlers Aweigh with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Antlers Aweigh is located above a Wintergreen hiking trail, making this home a great launch pad for all your mountain ad ...

    From $643 per night (USD)

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  • Cool Mountain Breezes on The Slopes- It's Pumpkin Spice Time!
    From $341 per night (USD)

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    Cool Mountain Breezes on The Slopes- It's Pumpkin Spice Time!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Your Wintergreen Resort adventure begins at this marvelous 3-bedroom home with a 2-levels of decks. With 2 king beds, 2 ...

    From $341 per night (USD)

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  • Mountain Inn Studio 93 with Wintergreen Advantage
    From $284 per night (USD)

    Expedia

    Mountain Inn Studio 93 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Inn Main-Floor King Retreat Enjoy a stylish and comfortable stay in this hotel-style guest room on the main fl ...

    From $284 per night (USD)

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  • 4 Bedroom mountain cabin in the relaxing Wintergreen Resort with AC & Fireplace
    From $527 per night (USD)

    VRBO

    4 Bedroom mountain cabin in the relaxing Wintergreen Resort with AC & Fireplace

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Heaven on 11 is a comfortable 4 BR / 3 BA house with 3 Queen Beds, and a Twin trundle bed, sleeps 8, with two bedrooms o ...

    From $527 per night (USD)

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  • Newly Built Designer Home in Wintergreen
    From $419 per night (USD)

    Expedia

    Newly Built Designer Home in Wintergreen

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Welcome to Onyx Hill, a custom built 4-bedroom, 3.5-bathroom home nestled within the picturesque Wintergreen Resort! Eve ...

    From $419 per night (USD)

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  • Northridge 07 With Wintergreen Advantage
    From $339 per night (USD)

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    Northridge 07 With Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Mountain Retreat in Northridge Escape to the mountains in this 1-bedroom, 2-bath condo in Northridge, located in Winter ...

    From $339 per night (USD)

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  • Dobie 24 with Wintergreen Advantage
    From $731 per night (USD)

    Expedia

    Dobie 24 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Dobie Spacious Mountain Getaway Experience a relaxing Wintergreen getaway in this spacious 3-bedroom, 3-bath condo at D ...

    From $731 per night (USD)

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  • Almost Heaven
    From $676 per night (USD)

    VRBO

    Almost Heaven

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    7

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

    From $676 per night (USD)

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  • Trail Magic- Sk-in & Ski-out
    From $555 per night (USD)

    Expedia

    Trail Magic- Sk-in & Ski-out

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Summary: Trail Magic | Ski-In/Ski-Out Lodge at Wintergreen Resort with Hot Tub Experience the magic of the mountain ...

    From $555 per night (USD)

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  • All Downhill From Here
    From $239 per night (USD)

    VRBO

    All Downhill From Here

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    <p>Enjoy everything you need atop Virginia's <strong>Wintergreen Resort</strong>. This newly renovated condominium is lo ...

    From $239 per night (USD)

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  • Highlands 24 with Wintergreen Advantage
    From $667 per night (USD)

    Expedia

    Highlands 24 with Wintergreen Advantage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Highlands Spacious Mountain Retreat Escape to the peaceful mountain setting of this spacious 3-bedroom, 3-bath condo in ...

    From $667 per night (USD)

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  • Gum Tree #1 with Wintergreen Advantage
    From $338 per night (USD)

    VRBO

    Gum Tree #1 with Wintergreen Advantage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Relaxing Mountain Escape at Wintergreen Resort Enjoy a peaceful getaway in this 1-bedroom, 1-bath condo at Wintergreen ...

    From $338 per night (USD)

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  • Wintergreen Luxury, Best Views in VA!
    From $1204 per night (USD)

    Expedia

    Wintergreen Luxury, Best Views in VA!

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    16

    Welcome to Blackrock Manor, a one-of-a-kind luxury chalet in Wintergreen that sleeps 16. Experience spectacular mountain ...

    From $1204 per night (USD)

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  • Ledges   66 with Wintergreen Advantage
    From $507 per night (USD)

    VRBO

    Ledges 66 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Ledges Mountain Getaway Make yourself at home in this 2-bedroom, 2-bath condo in Ledges, nestled in Wintergreen's sceni ...

    From $507 per night (USD)

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  • Vistas 87  with Wintergreen Advantage
    From $359 per night (USD)

    Expedia

    Vistas 87 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Vistas Cozy Mountain Escape Enjoy a peaceful getaway in this 1-bedroom, 2-bath condo in Vistas, nestled in Wintergreen' ...

    From $359 per night (USD)

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  • Vistas 75  with Wintergreen Advantage
    From $360 per night (USD)

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    Vistas 75 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Vistas Mountain Retreat Escape to the mountains in this 1-bedroom, 2-bath condo in Vistas, located in Wintergreen's sce ...

    From $360 per night (USD)

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  • Overlook 08  with Wintergreen Advantage
    From $501 per night (USD)

    Expedia

    Overlook 08 with Wintergreen Advantage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Overlook Mountain Getaway Unwind in this 2-bedroom, 2-bath condo in Overlook at Wintergreen Resort, nestled in the scen ...

    From $501 per night (USD)

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    Details