A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Wintergreen vacation rentals

A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.

1. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (60 reviews)
"Nice resort"
United States
Diana J.
The price is AED 296
AED 787 total
includes taxes & fees
6 Oct - 7 Oct
Where the Trail Ends
A wooden deck with a round table and chairs, overlooking a grassy area with trees.

2. Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (129 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is AED 426
AED 912 total
includes taxes & fees
30 Sep - 1 Oct
Escape to the Blue Ridge Mountains at Wine-tergreen!
A garden with a variety of flowers and trees at dusk.

3. New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (161 reviews)
"It was a beautiful stay - we enjoyed the place and wished we could have stayed one more day to soak up the surroundings of the area more!"
United States
Michelle W.
The price is AED 404
AED 887 total
includes taxes & fees
30 Sep - 1 Oct
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A room with a wooden floor, a table with two stools, and a view through large windows with blinds.

4. Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (36 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
The price is AED 331
AED 767 total
includes taxes & fees
30 Sep - 1 Oct
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

5. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (37 reviews)
"Great place to stay for our family of 4 for a wedding weekend. Easy check-in and close to the Inn."
United States
Scott M.
The price is AED 419
AED 945 total
includes taxes & fees
30 Sep - 1 Oct
Wintergreen Condo -Steps to Ski and restaurants
Private kitchen

6. "Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
United States
Amy K.
The price is AED 380
AED 1,087 total
includes taxes & fees
30 Sep - 1 Oct
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A two-story house with a stone foundation, a large front porch, and a chimney.

7. Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (124 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
The price is AED 466
AED 977 total
includes taxes & fees
30 Sep - 1 Oct
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
A two-story wooden cabin with a wooden deck and a small porch.

8. Walk to Market/Private community outdoor pool!

Walk to Market/Private community outdoor pool!
Wintergreen Resort
9.8 out of 10, Exceptional, (85 reviews)
"Great location. Enjoyed our stay."
United States
Alice W.
Walk to Market/Private community outdoor pool!
A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.

9. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (48 reviews)
"Wonderful stay, wonderful place!! The view, the fireplace, well appointed, comfortable bed, comfortable furniture, very clean...will definitely stay again! Thank you!!"
United States
Art P.
The price is AED 511
AED 1,027 total
includes taxes & fees
30 Sep - 1 Oct
Panoramic Peak: Wintergreen Condo with Views
A mountainous landscape with dense green forests and a clear sky.

10. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (333 reviews)
"Our 2-BR condo was lovely. Everything was sparkling clean and the place was spacious for what we needed. What MADE it, though, was the VIEW which was spectacular! I felt we should have been pre-informed that there was no coffee for us to use. We could have easily brought some but didn’t know of its non-existence."
United States
Virginia
The price is AED 344
AED 860 total
includes taxes & fees
30 Sep - 1 Oct
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

11. Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (60 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
Spacious + Serene Mtn Top Escape, 4 En Suites
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

12. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (37 reviews)
"Great stay for my family!"
United States
Joel M.
The price is AED 364
AED 903 total
includes taxes & fees
30 Sep - 1 Oct
Updated! Cozy and clean two bedroom condo.
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

13. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
The price is AED 349
AED 1,011 total
includes taxes & fees
4 Oct - 5 Oct
Three Little Bears
A cabin with a large window, surrounded by trees.

14. Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (35 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
The price is AED 555
AED 1,325 total
includes taxes & fees
7 Oct - 8 Oct
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A modern living room with a grey sofa set, a coffee table, and a fireplace.

15. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (15 reviews)
"Relaxing, scenic, quiet during the week, clean, modern, great communication with the host."
United States
Darlene
The price is AED 511
AED 1,027 total
includes taxes & fees
30 Sep - 1 Oct
Mountain View Vista: Resort Condo w/ Views
A swimming pool surrounded by lush greenery and a wooden cabin.

16. 2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.

2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
Wintergreen Resort
10.0 out of 10, Exceptional, (4 reviews)
"This is a warm and inviting condo. We enjoyed our stay. The host provided excellent communication!"
United States
Shannon T.
The price is AED 423
AED 1,176 total
includes taxes & fees
30 Sep - 1 Oct
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
A house with a covered patio, sliding glass doors, and a small outdoor seating area with chairs.

17. Mountain Retreat in Wintergreen!

Mountain Retreat in Wintergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
The price is AED 459
AED 1,001 total
includes taxes & fees
30 Sep - 1 Oct
Mountain Retreat in Wintergreen!
A two-story log cabin with a balcony, a staircase, and a snow-covered roof.

18. Pet-Friendly Retreat Walk to Slopes & Village!

Pet-Friendly Retreat Walk to Slopes & Village!
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place to stay comfortable beds. The place was nice and clean "
United States
Denise P.
The price is AED 444
AED 1,060 total
includes taxes & fees
12 Oct - 13 Oct
Pet-Friendly Retreat Walk to Slopes & Village!
A cozy living room with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.

19. Bide-a-Wee- Hike the Trails! Close to the slopes!

Bide-a-Wee- Hike the Trails! Close to the slopes!
Wintergreen Resort
9.2 out of 10, Wonderful, (12 reviews)
"Great house close to the village, would stay here again."
United States
David B.
The price is AED 622
AED 1,428 total
includes taxes & fees
12 Oct - 13 Oct
Bide-a-Wee- Hike the Trails! Close to the slopes!
A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

20. Luxury Condo in the Sky! Finest in Wintergreen!

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"Views from the porch are beautiful!Essentials ar all there Well thought out for a rentalHope to be back for another anniversary"
United States
rodney f.
Luxury Condo in the Sky! Finest in Wintergreen!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wintergreen Hotel Reviews

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

10/10 Excellent
"Amazing property and owners"
Francis B. 1-night trip
Posted 10 hours ago
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Frequently asked questions

Can I find vacation rentals in Wintergreen?

Yes, there are vacation rentals close to the most popular points of interest in Wintergreen, or you can select a secluded option if you'd like a relaxing place to stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffeehouses during your trip.

What are some of the best vacation rentals that Wintergreen has to offer?

Wintergreen cabin, hot tub, sauna, walk to trails: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Wintergreen are Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 and Remodeled 3BR/2BA Ski Chalet off Tyro Slope.

How many vacation rentals are there in Wintergreen?

Choose from 232 Expedia vacation rentals in Wintergreen for a memorable vacation.

What can I see and do in Wintergreen?

While you're exploring the area, George Washington National Forest and Humpback Rocks are a couple of picturesque spots to get outside and enjoy nature. While here, Bold Rock Hard Cider Nellysford Cidery and Wintergreen Resort are other places worth a visit.

What’s a vacation rental in Wintergreen like?

A vacation rental is a private property where you can stay for several days or longer in Wintergreen. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.