Vacation Rentals & Houses in Wintergreen

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16 houses

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Cozy Wintergreen Mountain Condo - King bed/dog friendly

Wintergreen condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$144

2BR Walkout Condo Private and Cozy!

Wintergreen apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Golf within 30mins drive

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Price per night from

$138

Great rentals within 20 miles that match your search

Rose Cottage at Steeles Tavern

Lexington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$230

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

Montebello log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 11

Match: Golf within 30mins drive

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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

Match: Golf within 30mins drive

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Price per night from

$1,949

Cottage at Massies Mill & the Blue Ridge Mountains

Massies Mill cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$172

Pine Creek Tiny House

Amherst house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Golf within 30mins drive

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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: Golf within 30mins drive

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Price per night from

$224

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

Afton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Golf within 30mins drive

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Price per night from

$287

Enjoy Mountain Living at the Woolly Bull Château

Roseland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$206

Howl at the Moon Farm and Cabin

Charlottesville log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$286

Paradise Mountain Estate

Greenwood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$275

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

Nellysford house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Golf within 30mins drive

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Price per night from

$264

Blueberry Hill Farm in Historic Shenandoah Valley

Spottswood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Excellent "headquarter" for exploring Shenandoah” We stayed for a week and was very satisfied with both location and the room and its facilities. Their was always a nice place to sit outside and enjoy the landscape or read regardless of the weather - either on the lawn or on the porch. We were primarily interested in hiking in the surrounding mountains and visiting historic sites and for that it was a perfect "headquarter" for the week we stayed.

Match: Golf within 30mins drive

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Price per night from

$126

The Lodge in Sugar Hollow

Crozet house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Golf within 30mins drive

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Price per night from

$458

Lovingston Get-Away

Lovingston apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$126

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