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Vacation Rentals & Houses in Wintergreen

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76 houses

Designer Home w/ Fire Pit, 70 Steps to Slopes!

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 3 hours 21 minutes

Price per night from

$385

Wintergreen Home w/ Hot Tub, Deck & Mountain Views

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

Price per night from

$237

Tyro Slope-Side House Ski In/Out Yr Rnd Views w/AC

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 58 minutes

Price per night from

$241

Cozy, Clean and Convenient Mountain Condo - King Bed & Dog Friendly

Wintergreen condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 55 minutes

Price per night from

$155

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!

Responds fast! avg. 2 hours 26 minutes

Price per night from

$338

Dogwood Haven

Wintergreen apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$191

The Retreat at Wintergreen

Wintergreen house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 58 minutes

Price per night from

$455

2BR Walkout Condo Private and Cozy!

Wintergreen apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$138

Wintergreen Condo w/ Mtn Views & Shuttle to Resort

Wintergreen condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$133

Wintergreen Resort Mountain Condo w/ Pool Access!

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

Price per night from

$107

Updated Condo w/ Deck - 1 Mi to Wintergreen Resort

Wintergreen condo

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$273

Mountaintop Wintergreen Resort Home w/ Deck+Views!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 21 minutes

Price per night from

$201

Cozy Mountain Retreat with Radiant Floor Heat - Dog Friendly

Wintergreen house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$144

Wintergreen Resort Home w/ Deck - 0.4 Mi to Slopes

Wintergreen house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 21 minutes

Price per night from

$414

Upscale Wintergreen Resort Home w/Golf Course View

Wintergreen house

5 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 3 hours 21 minutes

Price per night from

$194

Pet-Friendly Wintergreen Home w/ Deck!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 21 minutes

Price per night from

$266

Cozy Wintergreen Cabin Near Mountain Inn & Slopes!

Wintergreen cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

Price per night from

$166

Lavish Wintergreen Home w/Hot Tub by Skiing!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 21 minutes

Price per night from

$335

Wintergreen Resort Cabin w/Deck-Small Dogs Allowed

Wintergreen cottage

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$237

Blue Ridge Home with Mtn Views & On-Site Skiing!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 3 hours 21 minutes

Price per night from

$237

Prvt Cabin w/Hot Tub, Mins to Wintergreen Rst

Wintergreen cottage

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$273

Ski-In Ski-Out Wintergreen Condo w/Balcony

Wintergreen condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 21 minutes

Price per night from

$125

NEW! Cozy Wintergreen Resort Home w/ Fire Pit!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$208

Wintergreen Resort Cabin w/ 2 Decks & Hot Tub!

Wintergreen cottage

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$249

Mountain Escape: < 1 Mi Walk to Wintergreen Resort

Wintergreen house

6 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 3 hours 21 minutes

Price per night from

$308

Wintergreen Home w/ Deck - Near Skiing & Hiking!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$119

Peaceful Getaway w/ Fire Pit & Views: Ski & Hike!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$355

NEW! Blue Ridge Mtn Getaway in Wintergreen Resort!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 3 hours 21 minutes

Price per night from

$225

Bright Wintergreen Resort Home; Deck & Grill!

Wintergreen house

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 21 minutes

Price per night from

$325

NEW! Cozy Couples Getaway: Ski-In, Ski-Out Condo!

Wintergreen condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 21 minutes

Price per night from

$112

Wintergreen Family Ski Retreat w/ Fireplace & View

Wintergreen cottage

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 3 hours 21 minutes

Price per night from

$295

Wintergreen Resort Home w/ 2 Decks & New Hot Tub

Wintergreen house

3 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 3 hours 21 minutes

Price per night from

$166

NEW! Wintergreen Resort Condo: Walk to Ski Lifts!

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 21 minutes

Price per night from

$101

NEW! Cottage < 10 Mi to Wineries, Skiing & Hiking

Wintergreen cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 21 minutes

Price per night from

$112

Spacious Wintergreen Resort Home w/ Hot Tub!

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 3 hours 21 minutes

Price per night from

$302

NEW! Wintergreen Resort Home: 2 Decks + Ski Access

Wintergreen house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 21 minutes

Price per night from

$225

A-Frame Cabin w/Grill, Steps to Wintergreen Slopes

Wintergreen cottage

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$180

Cozy 'Hillside Hideaway' in Wintergreen Resort!

Wintergreen cottage

5 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 21 minutes

Price per night from

$250

Viewing 38 of 76
rentals in Wintergreen

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About Wintergreen

Wintergreen, Virginia is busy all year round &ndash; 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 &ndash; 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 &ndash; 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 &ndash; 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&rsquo;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
Wintergreen Resort 2 BR 2 BA Condo with LOW Rates
Great condo

Condo unit was very comfortable and is larger than it appears in the pictures. Easy to get to and parking close by. Area was very quite great for looking at nature. Would definitely stay there again. … see more
Tyro Slope-Side House Ski In/Out Yr Rnd Views w/AC
Great place

This place worked well for our two family ski vacation. We loved being able to ski in and out. The kitchen was well stocked. The fireplace was so cozy. … see more

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