Vacation Rentals & Houses in Wintergreen

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Chesapeake Bay Beach House in Reedville Virginia

Reedville house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$687

Find unspoiled natural beauty, slower pace and genuine southern hospitality...

Cape Charles house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$221

Old World Charm, Immaculate Potomac River Woodland Cottage, Polite Pets OK

Piney Point house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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Price per night from

$201

Stay on Historic Gloucester Main Street!

Gloucester condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$155

Kingsbay 'Bayhouse' Vacation Rental

Marion Station house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,140

Servants' Cottage on Huge Horse/Cattle Farm

Charlottesville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths

Cambridge house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 18

“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.

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Price per night from

$1,030

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Price per night from

$1,088

Pond House on Huge Horse Farm

Charlottesville cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

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Price per night from

$252

Sloop Creek Cottage

Reedville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$315

Shenandoah Crossing Resort August 31 thru Sept 7th 2019 Cabin rental

Gordonsville log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$201

Mimosa Cottage on Tangier Island

Tangier Island house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$201

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Price per night from

$1,088

Sleeps 12 - Large 4BR Townhome, Indoor/Outdoor Pool, Golf, Close To Theme Parks!

Williamsburg condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$549

Spacious 3BR Cottage - Family Friendly Resort - Close to Theme Parks

Williamsburg condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$260

Family Friendly Resort Cottage - Sleep 6 - Close to Theme Parks & Attractions

Williamsburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$260

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Price per night from

$260

Responds fast! avg. 3 hours 13 minutes

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Price per night from

$1,717

Kingsbay Dockside

Marion Station house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,088

Luxury Living in Richmond City

Richmond apartment

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$264

Where you want to be

Onancock apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

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Price per night from

$138

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Price per night from

$221

Massanutten Resort & Waterpark 2-bedroom condo, sleeps 8, w/loft and fireplace

Massanutten condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$86

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Price per night from

$144

Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16

Cambridge house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 18

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Price per night from

$859

Milker's Cottage - Horses in the Bach Yard

Gordonsville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$252

Traditional Bungalow 9

Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$258

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Price per night from

$221

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Price per night from

$445

Nautical Farmhouse Near Reedville/Smith Point Marina in Northern Neck VA

Reedville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$229

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