Vacation Rentals & Houses in Wintergreen

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133 houses

Responds fast! avg. 3 hours 10 minutes

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$83

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

Massanutten townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$155

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

Massanutten condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$207

Close to Williamsburg attractions. Plus, see all the amenities! 3bd, 3ba condo

Williamsburg apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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$241

Servants' Cottage on Huge Horse/Cattle Farm

Charlottesville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$173

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

$1,032

Kingsgate- Family Fun in Colonial Williamsburg!

Williamsburg condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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$493

Regal Vistas at Massanutten Resort Rental

Massanutten villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$402

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

Williamsburg condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

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$402

Old Wagon Lodge In Shenandoah Woods

Luray house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

“Relaxing!” We had a wonderful time!The game room was awesome. The cabin was nice and clean. Everything we needed was provided. We live in Hampton Roads, which is very busy and noisy,so to be on top of a mountain,and the only sounds were that of nature was a welcome change. We were very close to Luray Caverns, and the local Food Lion. We spent Saturday hiking in the woods around the cabin. Just loved it! The locals were the epitome of southern hospitality. I highly recommend Old Wagon Lodge. :)

Responds fast! avg. 2 hours 3 minutes

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$243

The Colonies at Williamsburg - June 28-July 5

Williamsburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$230

A Shenandoah Valley View - Luxury Home

Massanutten house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 43 minutes

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$356

Rental home Shenandoah river. Secluded 160 acres

Shenandoah house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$689

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

Gordonsville log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$201

Pet-Friendly Shenandoah Retreat- Hot Tub, Fast Wi-Fi, Gorgeous Views!

Luray lodge

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 3 minutes

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$348

The Legends Getaway

Bryantown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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$603

Williamsburg Plantation 2 bedroom suite with full kitchen

Williamsburg villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 21 minutes

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$201

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$459

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

Massanutten condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$86

Stylish Oasis in the west end of Richmond

Henrico villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$574

Cozy Mountain Song- Massanutten Mountain

Massanutten log cabin

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 3 minutes

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$308

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Fox Den near Massanutten

McGaheysville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$316

Pond House on Huge Horse Farm

Charlottesville cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

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$253

Patrick Henry Square - 2BR/2BA Close to Colonial Williamsburg!

Williamsburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 24 minutes

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$184

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

Massanutten townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$345

Milker's Cottage - Horses in the Bach Yard

Gordonsville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

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$253

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Price per night from

$1,091

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

$861

Charlottesville, 1830's Row-house 1 Block from Downtown Pedestrian Mall

Charlottesville house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 9

Responds fast! avg. 28 minutes

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Price per night from

$688

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Price per night from

$1,091

Chesapeake Bay Beach House in Reedville Virginia

Reedville house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$689

Spotted Fawn Cabin - Luxury Rental Cabin

Shenandoah log cabin

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 50 minutes

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Price per night from

$339

Lake Getaway (paddle boards included)

Mineral house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 13 minutes

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Price per night from

$402

The Colonies at Williamsburg 4-Bedroom, 4 Baths, Sleeps 12, 2 Full Kitchens

Williamsburg condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

“Great accommodation with lovely outdoor pool for children” Great location. Good kitchen facilities with useful washing machine. Food Lion less than 5 minutes away made breakfast easy. Easy access to main road with restaurants etc. 15 mins to colonial Williamsburg and then less than 30 to Jamestown and Yorktown. Helpful reception and free racket hire for tennis courts. All round a great place to stay with young and older children. Everyone friendly and everything very clean. Kids loved slides and basketball hoops in the pools and that made the holiday for us.

Responds fast! avg. 2 hours 26 minutes

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Price per night from

$407

King's Creek Plantation: 1-Bedroom / Sleeps 4 / Full Kitchen

Williamsburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 26 minutes

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Price per night from

$144

Westhampton Guest House

Richmond guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$155

Newly Renovated Lake Access Home with Hot Tub and Boat Slip

Mineral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$173

Romantic River Front Cabins

Luray log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

“Perfect Getaway” We absolutely loved this cabin and use it as the standard against which to judge all other rentals we consider. The cabin was spotless and quaint. We loved stargazing, exploring the creek behind the cabin, attempting to canoe, and cooking chicken in the fire ring. There is a charcoal girll available but we stayed so busy we didn't get a chance to use it. The electric fireplace in the bedroom kept us warm all night and our cat absolutely loved the cute loft. I absolutely recommend anyone considering staying in a cabin in Luray to come here. The grounds were so quiet and it was a quick drive to the Virginia Museum of the Civil War in New Market as well as the beautifully scenic drive in the Blue Ridge Mountains. We came here for our anniversary trip and we had the best time. Even 2 years onward we can't stop raving about it. We made the best memories here and would love to come again if we were ever in Virginia. This cabin is absolute perfection.

Responds fast! avg. 3 hours 49 minutes

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Price per night from

$212

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