Vacation Rentals & Houses in Wintergreen

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23 houses

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Cozy Wintergreen Mountain Condo - King bed/dog friendly

Wintergreen condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children under 5

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Price per night from

$144

July Available: Luxury Mountain House on Golf Course w/ Resort Membership

Wintergreen house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

“Mountain Resort in Va” Cozy ski getaway or family retreat. Soaring wood ceilings and stone fireplace; huge windows. Lovely views of lush green lawn and several tall trees. Peaceful and quiet. Huge kitchen and dining area, full amenites, and very clean. You will love it! It is also perfect for 2-3 couples with 3 1/2 baths and 3 private bedrooms. The master suite is gorgeous!

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Price per night from

$338

2BR Walkout Condo Private and Cozy!

Wintergreen apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$138

Cozy Condo in Wintergreen Resort Just 3 Minutes Walk To Slopes Restaurants

Wintergreen condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$109

Breathtaking luxury rental

Wintergreen house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$3,213

Great rentals within 20 miles that match your search

Rock-n-Creek Cabin mile post 27 off BR Pkwy

Montebello log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 11

Match: Children under 5

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Price per night from

$270

Maren Estate (Mountain Estate 20 min to UVA)

Afton house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$1,951

Cottage at Massies Mill & the Blue Ridge Mountains

Massies Mill cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$172

Pine Creek Tiny House

Amherst house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Children under 5

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Price per night from

$171

Second Creek Farm near Blue Ridge Parkway in Virg

Montebello house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$224

Rose Cottage at Steeles Tavern

Lexington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children under 5

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Price per night from

$229

Mountain Retreat Nestled in the Virginia Foothills

Charlottesville house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$401

Big bronze house in Waynesboro

Waynesboro house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Children under 5

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Price per night from

$224

The Lodge in Sugar Hollow

Crozet house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Children under 5

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Price per night from

$458

Howl at the Moon Farm and Cabin

Charlottesville log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$286

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Price per night from

$178

The Blue Ridge Blue Lllama | Minutes to 151 | Pets OK | Hikes, Brews and Wine

Nellysford house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Children under 5

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Price per night from

$264

Enjoy Mountain Living at the Woolly Bull Château

Roseland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$205

Paradise Mountain Estate

Greenwood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$275

Farm Cottage in the Heart of Virginia's Wine Country!

Afton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$287

Stylish Farmhouse

Roseland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$241

Cozy cabin, perfect for couples or the single traveler!

Schuyler house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Children under 5

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Price per night from

$172

Spacious house located in Shenandoah Valley

Waynesboro house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$103

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