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Vacation Rentals & Houses in Wintergreen

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Vacation Rentals & Houses in Wintergreen

About Wintergreen

89 houses

NEW! Updated Wintergreen Resort Home w/Mtn. Views!

Wintergreen house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 8 minutes

Price per night from

$205

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Central Wintergreen Home - 70 Steps to Ski Slopes!

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 11 minutes

Price per night from

$346

1 / 39

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

Wintergreen log cabin

2 bedrooms / 1 bathroom / sleeps 4

“Great get away for us and our dog!” Wonderful cabin, great location! Cabin was spotless, and well appointed. Loved the gas fireplace and screened porch. Can't wait to return to Cabin Creekwood!

Responds fast! avg. 3 hours 0 minutes

Price per night from

$148

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

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 25 minutes

Price per night from

$190

1 / 23

Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood

Wintergreen house

3 bedrooms / 1 bathroom / sleeps 8

“Great mountain getaway!” Conveneintly located near Wintergreen Resort, this is an awesome way to enjoy snowboarding and sking. The cabins are quaint and cozy and the owners are very nice. Especially their Jack Russell Toby! He visits every cabin eve

Responds fast! avg. 3 hours 0 minutes

Price per night from

$148

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

Wintergreen condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$89

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Simple Pleasures -N Ridge - Holidays Upon Us

Wintergreen apartment

3 bedrooms / 3 bathrooms / sleeps 7

“Wonderful” The accommodations beautiful, Simple Pleasures North Ridge Holidays Upon Us, great location, good food, great skiing for grandkids [first time], son and wife. I would definitely recommend this rental to anyone; it was absolutely stocked w

Responds fast! avg. 2 hours 2 minutes

Price per night from

$150

1 / 46

Wintergreen Studio w/ 4th of July Fireworks Views!

Wintergreen studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 11 minutes

Price per night from

$85

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The Bear Dance Cabin at Wintergreen

Wintergreen log cabin

3 bedrooms / 2 bathrooms / sleeps 6

“Very nice accomidations, close to resort & slopes” The cabin is adorable & cozy. Even though it has a cabin feel, the bathrooms and kitchen are very nice and you don't feel like you're "roughing it" at all. The place a newer build, so it feels very cl

Responds fast! avg. 57 minutes

Price per night from

$175

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July 9 Week Available: Luxury Mountain House 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

Responds fast! avg. 2 hours 29 minutes

Price per night from

$275

1 / 13

Dogwood Haven

Wintergreen apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$149

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Fit for a KING ( king size beds!)

Wintergreen house

5 bedrooms / 4 bathrooms / sleeps 10

“Great!” The process of reserving, paying, getting in the house and out of the house was easy and fool-proof!! The house was amazing and the location was perfect. Dawn (the contact for the house) was the most helpful and thoughtful person you could

Responds fast! avg. 34 minutes

Price per night from

$422

1 / 68

TREELOFT- in the snow drift!

Wintergreen house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

Price per night from

$388

1 / 14

Wintergreen - Slope Side w/ Resort Pass

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful views, clean and comfortable condo.” We loved our stay at this condo. The view from the back deck was beautiful. We enjoyed a bit of hiking, the Zip-line, nearby Monoccan lake, family time, cooking in, and eating at area restaurants. Would c

Responds fast! avg. 1 hour 47 minutes

Price per night from

$99

1 / 11

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

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$100

1 / 15

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

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$100

1 / 16

'5 Peaks' Luxury Wintergreen Resort Home w/Hot Tub

Wintergreen house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 6 minutes

Price per night from

$225

1 / 38

Cozy Custom Home in Wintergreen Resort Area!

Wintergreen house

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 6 minutes

Price per night from

$265

1 / 33

NEW! Cozy Wintergreen Resort Home - Walk to Lifts!

Wintergreen townhouse

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 8 minutes

Price per night from

$140

1 / 24

2BR Walkout Condo Private and Cozy!

Wintergreen apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 19 minutes

Price per night from

$125

1 / 19

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

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$170

1 / 16

3BR Wintergreen House w/Private Decks!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 11 minutes

Price per night from

$185

1 / 22

NEW! Modern Wintergreen Farmhouse - 1 Mi to Resort

Wintergreen condo

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 8 minutes

Price per night from

$245

1 / 24

Chestnut Place Mountain Lodge

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 15

Responds fast! avg. 34 minutes

Price per night from

$546

1 / 24

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

Wintergreen house

5 bedrooms / 6 bathrooms / sleeps 13

Responds fast! avg. 34 minutes

Price per night from

$545

1 / 41

The Mountain House

Wintergreen house

5 bedrooms / 3 bathrooms / sleeps 12

“A wonderful stay” Our family traveled to Barbara's home to enjoy a relaxing getaway and celebrate a college graduation! The house is equipped with everything you need- comfortable beds and immaculate. I would give it a 5.- and know that we will look

Responds fast! avg. 2 hours 32 minutes

Price per night from

$275

1 / 9

The Retreat at Wintergreen

Wintergreen house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 1 minutes

Price per night from

$395

1 / 21

22 Tyro - Luxury Ski In/Out Mountain Home on Upper Tyro Slope

Wintergreen house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$500

1 / 26

Mountain Escape in the Spring

Wintergreen apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 28 minutes

Price per night from

$110

1 / 17

Cabin at Wintergreen - VA Mt. Resort Luxury Rental

Wintergreen house

5 bedrooms / 3 bathrooms / sleeps 10

“All we needed in a cabin for a great weekend getaway.” This place was great! I took a group of young adults from my church, and they were all impressed with the house. They kept asking me, "Where did you find this place?" The cabin feels very rustic a

Price per night from

$400

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Peaceful Roseland House w/ Loft, Deck & Mtn Views!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 11 minutes

Price per night from

$285

1 / 24

A Cajun Chalet

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

Price per night from

$447

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NEW! Wintergreen Condo w/Views & Shuttle to Resort

Wintergreen condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 8 minutes

Price per night from

$140

1 / 24

Mountain Retreat

Wintergreen house

5 bedrooms / 7 bathrooms / sleeps 8

Price per night from

$348

1 / 9

Mountaintop Lodge, Wintergreen Resort

Wintergreen house

9 bedrooms / 10 bathrooms / sleeps 24

Price per night from

$1,460

1 / 34

NEW! Cozy Wintergreen Resort Condo w/ Pool Access!

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 6 minutes

Price per night from

$105

1 / 23

Family & Dog Friendly Spacious Mountain Home

Wintergreen house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$400

1 / 23

ALMOST HEAVEN AT WINTERGREEN RESORT!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

Price per night from

$390

1 / 29
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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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