Vacation Rentals & Houses in Wintergreen

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Avon House in Historic Downtown near the mall, UVA, restaurants & free trolley

Charlottesville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$1,262

LeFay Cottage at Little Washington

Washington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden Golf course on site or within 15 min walk

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Price per night from

$602

Cozy King Size Bed 2nd Floor (Apt. 2)

Norfolk apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$85

Richmond - Ashland Gem / Minutes to I95

Ashland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$213

Beautiful home 15 minutes from Downtown/ VCU

Ampthill house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden Golf course on site or within 15 min walk

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Price per night from

$115

Bahia Breeze - Beachfront Cottage

Chesapeake Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Match: Garden Golf course on site or within 15 min walk

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Price per night from

$226

SOLYMAR COTTAGE

Oak Grove house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$273

Spacious, historic Chincoteague Is. vacation house

Chincoteague Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$195

Kingsbay Cottage/Chalet

Marion Station house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$402

Hot fun in the summertime...bring family and friends...plenty of room

Williamsburg condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$402

Pet friendly family farmhouse on 28 private acres.

Quinton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Garden Golf course on site or within 15 min walk

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Price per night from

$461

Luxury Living in Richmond City

Richmond apartment

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$264

Mai Villa Hampton - Where Good Times Happen!

Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$458

Mountain Dreams*Luxury 4 Bedroom*HotTub*

Massanutten house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$320

Bear Cabin Mountain Retreat indoor Hot Tub, Games

McGaheysville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Garden Golf course on site or within 15 min walk

All filters match

Price per night from

$287

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Regal Vistas at Massanutten Resort Rental

Massanutten villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$402

Henrys Mountain Haven at Massanutten Resort

Massanutten house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$226

July 4 - 11; Regal Vista - Massanutten Resort in Virginia

Massanutten townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$344

Massanutten Resort Retreat - Ideal Villa For Large Group To Enjoy The Resort..

Massanutten villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$282

Traditional Bungalow 9

Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$258

Beach Bungalow East

Norfolk bungalow

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 2 hours 29 minutes

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$258

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

Williamsburg condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$550

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

Williamsburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$261

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

Williamsburg condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$261

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$366

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$419

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$366

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$261

Responds fast! avg. 3 hours 10 minutes

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$83

Governor's Green Resort 2br suite, Saturday check-in

Williamsburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$83

Governor's Green Resort 2br suite, Sunday check-in

Williamsburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$83

Summit at Massanutten Resort: 2BR/2BA/Full Kitchen.

Massanutten townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$155

Very Clean! Newly remodeled one bedroom with nature lake views

Williamsburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$188

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$144

Book New Year's 2021 at Massanutten Resort NOW! ONLY one left!

Massanutten condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$207

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

Massanutten condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$86

Blue Fox Chalet

McGaheysville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$316

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

Gordonsville log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Garden, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$201

Viewing 38 of 171
rentals in Wintergreen

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