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Vacation Rentals & Houses in Wintergreen

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Vacation Rentals & Houses in Wintergreen

About Wintergreen

85 houses

Mountaintop Resort-Center 3 Kings Twins PASSes

Wintergreen apartment

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 16 minutes

1 / 37

Wintergreen Resort 2 BR 2 BA Condo with LOW Rates

Wintergreen apartment

2 bedrooms / 2 bathrooms / sleeps 6

1 / 12

TREELOFT- in the snow drift!

Wintergreen house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 37 minutes

1 / 14

Chestnut Place Mountain Lodge

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 15

Responds fast! avg. 37 minutes

1 / 24

July 9 Week Available: Luxury Mountain House w/ Resort Membership

Wintergreen house

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 33 minutes

1 / 13

Secluded 2BR Pet-Friendly Cabin on Mountain Stream-Screen Porch

Wintergreen log cabin

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 42 minutes

1 / 20

Dogwood Haven

Wintergreen apartment

2 bedrooms / 1 bathroom / sleeps 4

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3BR Wintergreen House w/Private Decks!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 36 minutes

1 / 22

4 Season Mountain Inn Retreat

Wintergreen condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 54 minutes

1 / 23

Simple Pleasures -N Ridge - Holidays Upon Us

Wintergreen apartment

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 1 hour 48 minutes

1 / 46

Central Wintergreen Home w/ Free Resort Amenities!

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 36 minutes

1 / 39

CRAZY AMAZING get-a-way! (Crazy, in a GOOD way)

Wintergreen house

5 bedrooms / 6 bathrooms / sleeps 13

Responds fast! avg. 37 minutes

1 / 41

Fit for a KING ( king size beds!)

Wintergreen house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 37 minutes

1 / 68

Mountaintop Lodge, Wintergreen Resort

Wintergreen house

9 bedrooms / 10 bathrooms / sleeps 24

1 / 34

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

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

1 / 16

The Bear Dance Cabin at Wintergreen

Wintergreen log cabin

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 53 minutes

1 / 20

Ski-in/Ski-out Wintergreen House w/ Hot Tub!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 36 minutes

1 / 23

A Cajun Chalet

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 37 minutes

1 / 32

Wintergreen - Slope Side w/ Resort Pass

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 59 minutes

1 / 11

Up-On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

1 / 15

Cabin at Wintergreen - VA Mt. Resort Luxury Rental

Wintergreen house

5 bedrooms / 3 bathrooms / sleeps 10

1 / 24

Wintergreen Studio w/ 4th of July Fireworks Views!

Wintergreen studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 10 minutes

1 / 25

The Retreat at Wintergreen

Wintergreen house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 2 minutes

1 / 21

Down On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

1 / 16

Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood

Wintergreen house

3 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 2 hours 42 minutes

1 / 19

2BR Walkout Condo Private and Cozy!

Wintergreen apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 41 minutes

1 / 19

The Mountain House

Wintergreen house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 50 minutes

1 / 9

Cozy and Clean Resort Condo - New Ownership and listed for the first time!

Wintergreen condo

1 bedroom / 1 bathroom / sleeps 4

1 / 10

NEW! 4BR+Loft Roseland House - Deck w/ Mtn Views!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 36 minutes

1 / 24

NEW! Cozy Wintergreen Resort Condo w/ Pool Access!

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 36 minutes

1 / 23

Mountain Escape in the Spring

Wintergreen apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 28 minutes

1 / 17

Cozy Custom Home in Wintergreen Resort Area!

Wintergreen house

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 36 minutes

1 / 24

Mountain Retreat

Wintergreen house

5 bedrooms / 7 bathrooms / sleeps 8

1 / 9

NEW! Cozy Wintergreen Resort Home - Walk to Lifts!

Wintergreen townhouse

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 36 minutes

1 / 24

Family & Dog Friendly Spacious Mountain Home

Wintergreen house

4 bedrooms / 2 bathrooms / sleeps 10

1 / 23

WINTERGREEN MOUNTAIN HOUSE

Wintergreen house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 39 minutes

1 / 17

Top of the Resort (Discounted Rates Available)

Wintergreen house

6 bedrooms / 5 bathrooms / sleeps 14

1 / 24

wintergreen pet ski hot tub fireplace hike golf pool pets firepl

Wintergreen chalet

3 bedrooms / 2 bathrooms / sleeps 6

1 / 39
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About Wintergreen

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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.

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