Vacation Rentals & Houses in Wintergreen

Updating...

age 0-16
24 Results

Relevance

Price: low to high

Price: high to low

Reviews

24 houses

Cozy Wintergreen Mountain Condo - King bed/dog friendly

Wintergreen condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$144

July Available: Luxury Mountain House on Golf Course w/ Resort Membership

Wintergreen house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

“Mountain Resort in Va” Cozy ski getaway or family retreat. Soaring wood ceilings and stone fireplace; huge windows. Lovely views of lush green lawn and several tall trees. Peaceful and quiet. Huge kitchen and dining area, full amenites, and very clean. You will love it! It is also perfect for 2-3 couples with 3 1/2 baths and 3 private bedrooms. The master suite is gorgeous!

Price per night from

$338

2BR Walkout Condo Private and Cozy!

Wintergreen apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$138

Cozy Condo in Wintergreen Resort Just 3 Minutes Walk To Slopes Restaurants

Wintergreen condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$109

Breathtaking luxury rental

Wintergreen house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$3,195

Great rentals within 20 miles that match your search

Rose Cottage at Steeles Tavern

Lexington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$229

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

Montebello log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 11

Price per night from

$269

Cottage at Massies Mill & the Blue Ridge Mountains

Massies Mill cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$172

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.

Price per night from

$126

Big bronze house in Waynesboro

Waynesboro house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$223

Pine Creek Tiny House

Amherst house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$170

Maren Estate (Mountain Estate 20 min to UVA)

Afton house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Price per night from

$1,946

Second Creek Farm near Blue Ridge Parkway in Virg

Montebello house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$224

The Lodge in Sugar Hollow

Crozet house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$458

Mountain Retreat Nestled in the Virginia Foothills

Charlottesville house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$401

Enjoy Mountain Living at the Woolly Bull Château

Roseland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$205

Spacious house located in Shenandoah Valley

Waynesboro house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$103

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

Afton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$287

Howl at the Moon Farm and Cabin

Charlottesville log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$286

Lovingston Get-Away

Lovingston apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$126

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

Nellysford house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$264

Price per night from

$178

Stylish Farmhouse

Roseland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$241

Cozy cabin, perfect for couples or the single traveler!

Schuyler house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$172

×

About Wintergreen

Wintergreen, Virginia is busy all year round – there's plenty to do! You can try golfing, skiing, mountain climbing, hiking, biking and pretty much anything else you can think of.

You'll find this idyllic spot on the eastern side of the Blue Ridge Mountains, and be amazed at the spectacular views from your very own Wintergreen vacation rental – get searching on FlipKey, today!

About Wintergreen, Virginia

The area around Wintergreen was once populated by the Tuscarora Indians who lived near the Rockfish and James rivers. The Rockfish River Valley has some spectacular scenery and is well worth visiting.

Nearby Jamestown was the first permanent European settlement in the USA, founded by the British in 1607. Because of this, Wintergreen has lots of history to explore – try heading to one of the museums to find out more!

The food in Wintergreen is a mix of American and European (mainly Italian and French). You can eat a hearty steak, or more delicate seafood and fish. There's something for everyone, including vegans and vegetarians.

The area is also known for brewing delicious craft beers – some of the breweries have been going since colonial times. Try some during your stay.

What to do

At the Wintergreen Resort, there are two golf courses for enthusiasts, Devil's Knob and Stoney Creek. They're a great day out.

If you like walking, go along the Rockfish Valley Loop Trail system, and visit Spruce Creek Park. If you want something a bit more challenging, head up to the Appalachian Trail.

In winter you can go skiing, snowboarding and skate. But pack your thermals, as it can get a bit chilly.

Visit Williamsburg and see how people lived there in previous centuries. The town is a living history museum and is full of beautifully restored 17th and 18th century buildings.

The history of Virginia is closely linked to the Civil War. Visit the Appomattox court house, where General Robert E. Lee formally surrendered to General Ulysses S. Grant.

Go to Bold Rock and sample the delicious ciders. You get an amazing view over Wintergreen, and there's lots of space where dogs and kids can run free.

Lyndhurst, Virginia, is home to Humpback Rocks Visitor Center and Mountain Farm. Go to the top of Humpback Rocks and take in the majestic view.

Top Wintergreen travel tips

The easiest way of getting to Wintergreen is by car. You can fly to Charlottesville Albemarle airport, or to Dulles International Airport (IAD) and take a bus or shuttle service. Rent a car at the airport and drive to Wintergreen.

If you love nature's colors, go to Wintergreen in fall. Before you go, check the foliage report from the Department of Forestry. Crabtree Falls, on the Blue Ridge Parkway, is a wonderful place for a picnic.

Pick your own apples and pumpkins and buy butternut squash, cashews sweet potatoes and freshly pressed cider during your stay.

Don't leave the area without visiting Devils Backbone to sample the micro-brews.

Whenever you go to Wintergreen, Virginia, you’ll find plenty of activities to try. You can visit the Civil War battlefields, walk the Rockfish Valley Loop Trail, or go to see the historic buildings of Virginia.

Check out Wintergreen vacation rentals here on FlipKey and book your perfect stay.

Top Destination reviews

2BR Walkout Condo Private and Cozy!
Very comfortable, all the conviences of home with a great view of the golf course .

Perfect condo if you need two bed rooms, very comfortable with a great view of the tee on the golf course . Great place to relax . A lot of attractions, plenty of things to do while my husband was golfing. Went to the antique shops in the area and the Berry Farm Winery. We enjoyed he cider mills and the brewing companies. Would definitely stay there again, really enjoyed staying at the condo.see more
July Available: Luxury Mountain House on Golf Course w/ Resort Membership
Beautiful home and wonderful views

Very spacious home in a beautiful setting. Wonderful deck with view of golf course. So much provided by the owner [ paper towel, napkins, toilet paper, etc. ]. Enjoyed the wineries in the area. Was a great place for three couples to get together and relax. … see more

Also consider