Vacation Rentals & Houses in Wintergreen

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130 houses

Historic Powhatan Resort - Diamond Resort (Williamsburg, VA)

Williamsburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Jacuzzi or hot tub Sea view

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Price per night from

$287

Quiet Cottage, Hot Tub, Bay View, Block to Beach, 1hr to DC

Saint Leonard house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Jacuzzi or hot tub Sea view

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Price per night from

$252

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Incredible Ocean View in The North End of Virginia Beach

Virginia Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Sea view

1 of 2 filters match

Price per night from

$201

Beach Bungalow East

Norfolk bungalow

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 2 hours 29 minutes

1 of 2 match: Jacuzzi or hot tub, Sea view

1 of 2 filters match

Price per night from

$259

Spotted Fawn Cabin - Luxury Rental Cabin

Shenandoah log cabin

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 50 minutes

1 of 2 match: Sea view, Jacuzzi or hot tub

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Price per night from

$339

Cozy King Size Bed 1st Floor (Apt. 1)

Norfolk apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Jacuzzi or hot tub, Sea view

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Price per night from

$85

My Pan-O-Sea-A on the Chesapeake Bay.

White Stone cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Great View!” Loved the bedroom view, priceless! We could not have had a better view! Great place, very clean and has everything you could possibly need!

1 of 2 match: Jacuzzi or hot tub, Sea view

1 of 2 filters match

Price per night from

$230

Big & beautiful at the beach 2

Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Jacuzzi or hot tub, Sea view

1 of 2 filters match

Price per night from

$516

1 of 2 match: Jacuzzi or hot tub, Sea view

1 of 2 filters match

Price per night from

$108

Lake Getaway (paddle boards included)

Mineral house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 11 minutes

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$402

Chesapeake Bay Beach House in Reedville Virginia

Reedville house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Jacuzzi or hot tub, Sea view

1 of 2 filters match

Price per night from

$689

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

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

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

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$144

Westhampton Guest House

Richmond guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Sea view, Jacuzzi or hot tub

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Price per night from

$155

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.

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$213

Newly Renovated Lake Access Home with Hot Tub and Boat Slip

Mineral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$172

Williamsburg, VA: 2 BR Condo w/Pool, Near Historic Williamsburg & Busch Gardens

Williamsburg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$132

Family-Friendly Condos Near Historic Attractions w/ Two Pools & Mini Golf

Williamsburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$111

Family-Friendly Condos w/ Two Pools, Mini Golf, Nearby History & Full Kitchen

Williamsburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$132

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$91

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

Massanutten townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$155

Club Wyndham Governor's Green Resort

Williamsburg tower

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$201

The Legends Getaway

Bryantown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$603

Peak Retreat - Hot tub - Foosball table - Screened in Deck

McGaheysville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$327

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$459

The Madeline Cabin Nestled in the Shenandoah Mountains

Luray house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$218

Woodstone at Massanutten 2br suite, Saturday check-in

Massanutten condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$86

Woodstone at Massanutten 4BR suite Friday check-in

Massanutten condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$104

Woodstone at Massanutten 4BR suite Sunday check-in

Massanutten condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$104

Blue Fox Chalet

McGaheysville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$316

King's Creek Plantation 1br mini suite, Friday check-in

Williamsburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$69

The Farmhouse at Blue Rock

Washington house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,721

Woodstone at Massanutten 4BR suite Saturday check-in

Massanutten condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$104

King's Creek Plantation 1br mini suite, Thursday check-in

Williamsburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$69

Raspberry Retreat

Stanley house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$332

King's Creek Plantation 1br mini suite, Saturday check-in

Williamsburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$69

King's Creek Plantation 1br mini suite, Sunday check-in

Williamsburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$69

The Summit at Massanutten 2br suite, Friday check-in

Massanutten condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$83

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