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Vacation Rentals & Houses in Wintergreen

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92 houses

Wintergreen Home w/ Resort Passes, Steps to Slopes

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 4 minutes

Price per night from

$387

Updated Wintergreen Resort Home w/ Mountain Views!

Wintergreen house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 4 minutes

Price per night from

$224

Cozy, Clean and Convenient Resort Condo - Dog Friendly

Wintergreen condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 28 minutes

Price per night from

$114

Wintergreen Home w/ Hot Tub, Deck & Mountain Views

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$226

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 47 minutes

Price per night from

$196

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 everyday to welcome you home. We will definetly stay agian.

Responds fast! avg. 35 minutes

Price per night from

$172

The Mountain House

Wintergreen house

5 bedrooms / 3 bathrooms / sleeps 14

“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 forward to coming back!

Responds fast! avg. 18 minutes

Price per night from

$406

Wintergreen Home w/Private Decks - Walk to Resort!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$220

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

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect Condo at Wintergreen” Great condo, very peaceful and beautiful. Had everything one would need for a getaway to the mountains. Enjoyed the golf and antique shopping,

Price per night from

$116

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

$339

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

$115

Dogwood Haven

Wintergreen apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$175

Wintergreen Cabin w/Private Hot Tub, Deck & Views!

Wintergreen house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$214

Family Ski-In/Ski-Out Mountain Lodge on Upper Tyro Slope at Wintergreen w/Gas

Wintergreen house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 21 minutes

Price per night from

$575

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. 35 minutes

Price per night from

$172

2BR Walkout Condo Private and Cozy!

Wintergreen apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 28 minutes

Price per night from

$138

Slopeside Studio in Wintergreen - Ski-In/Ski-Out!

Wintergreen studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 4 minutes

Price per night from

$102

Chestnut Place Mountain Lodge

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 15

Responds fast! avg. 11 minutes

Price per night from

$632

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 clean and updated. It was super cozy, especially with the fireplace. We did have to turn the water on under the front porch when we arrived, which was a little odd, but I guess not really a big deal. It's a very short drive to the parking lot for Wintergreen. They said there was a shuttle but we never saw one the entire 3 days. Not a complaint since the drive is about 1 mile, just an FYI. The loft bedroom is high enough that it's still very private. It's also large enough to accommodate a blowup mattress for kids or an extra guest. The other 2 bedrooms are quite cozy & have there own heaters. I also loved that every bathroom had a heater so you can get it super warm & cozy for taking showers after a long day on the slopes. I would highly recommend this place for an authentic, yet nice & comfortable, mountain cabin stay! I would highly recommend this place.

Responds fast! avg. 2 hours 2 minutes

Price per night from

$203

'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

$279

The Retreat at Wintergreen

Wintergreen house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$459

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 imagine... anything you would be able to think of you mind need- she thought of... and was available the whole stay! Amazing experience.

Responds fast! avg. 11 minutes

Price per night from

$459

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

Wintergreen house

5 bedrooms / 6 bathrooms / sleeps 13

Responds fast! avg. 11 minutes

Price per night from

$639

Luxury Custom Home in Wintergreen Resort Area!

Wintergreen house

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 4 minutes

Price per night from

$315

Mountaintop Lodge, Wintergreen Resort

Wintergreen house

9 bedrooms / 10 bathrooms / sleeps 24

Price per night from

$1,480

Wintergreen Condo w/ Mtn Views & Shuttle to Resort

Wintergreen condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$139

Updated Condo w/ Deck - 1 Mi to Wintergreen Resort

Wintergreen condo

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$274

Wintergreen Resort Mountain Condo w/ Pool Access!

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$119

Wintergreen Resort Cabin - 0.7 Mi to Ski Mtn!

Wintergreen house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$173

Cozy Wintergreen Cabin Near Mountain Inn & Slopes!

Wintergreen cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$167

NEW! Cozy Wintergreen Resort Condo - Walk to Lift!

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 4 minutes

Price per night from

$137

Upscale Wintergreen Resort Home w/Golf Course View

Wintergreen house

5 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 4 minutes

Price per night from

$195

Wintergreen Resort Home w/ Golf Course View!

Wintergreen house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 4 minutes

Price per night from

$321

Wintergreen Retreat with Views - Walk to Ski Hill!

Wintergreen cottage

5 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 4 minutes

Price per night from

$172

Mountain Retreat

Wintergreen house

5 bedrooms / 7 bathrooms / sleeps 8

Price per night from

$465

Wintergreen Resort Home w/ Deck - 5 Min to Slopes!

Wintergreen house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 4 minutes

Price per night from

$374

J&K’s Mountain Escape

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$138

Mountaintop Wintergreen Resort Home w/ Deck+Views!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 4 minutes

Price per night from

$167

Viewing 38 of 92
rentals in Wintergreen

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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
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
Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood
Great cabin by a creek

The cabin was located by a creek, with a fireplace inside which took full advantage. The cabin was located close to wintergreen where we skied during day and spent quiet evenings playing cards or watching movies in front of fire. There was even several goodies for our dog. … 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
Down On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities
Nice cozy apartment

Fishy smell coming from the sink drain after we used it. We suspect that was from the previous tenants & not a regular issue with the apartment. … see more

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