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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Wintergreen vacation rentals

Fireplace

1. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (59 reviews)
"Wonderful location. Wonderful host. We will be back!"
United States
April S.
The price is AED 246
AED 734 total
includes taxes & fees
24 Aug - 25 Aug
Where the Trail Ends
Property grounds

2. 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, (158 reviews)
"We had a calm and relaxing mountain get a way. The property was charming and perfect for us, clean and organized. The location was great. We loved to go for walks nearby and visit the gnomes and fairies in the trees. We would love to make it an annual trip and would definitely stay here again."
United States
Michelle
The price is AED 404
AED 916 total
includes taxes & fees
11 Aug - 12 Aug
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Coffee/tea maker, fridge, microwave, oven

3. Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Wintergreen Resort
10.0 out of 10, Exceptional, (42 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is AED 380
AED 1,145 total
includes taxes & fees
11 Aug - 12 Aug
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Terrace/patio

4. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (36 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 433
AED 997 total
includes taxes & fees
11 Aug - 12 Aug
Wintergreen Condo -Steps to Ski and restaurants
Interior

5. 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, (33 reviews)
"Everything was perfect! "
United States
Danielle B.
The price is AED 331
AED 780 total
includes taxes & fees
11 Aug - 12 Aug
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
A mountainous landscape with dense green forests and a clear sky.

6. 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, (329 reviews)
"Awesome views and very clean condo! We had a very relaxing weekend!"
United States
Jordan O.
The price is AED 360
AED 912 total
includes taxes & fees
18 Aug - 19 Aug
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Condo, Private Bathroom (Mountain Vista View) | Lounge

7. Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
The price is AED 511
AED 945 total
includes taxes & fees
11 Aug - 12 Aug
Mountain View Vista
Outdoor dining

8. 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, (128 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is AED 426
AED 949 total
includes taxes & fees
11 Aug - 12 Aug
Escape to the Blue Ridge Mountains at Wine-tergreen!
Exterior

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

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
10.0 out of 10, Exceptional, (121 reviews)
"We loved staying at this apartment!"
United States
Sebastian A.
The price is AED 512
AED 1,058 total
includes taxes & fees
11 Aug - 12 Aug
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Property grounds

10. Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (117 reviews)
"Gorgeous views! We spent most of our time out and about, but enjoyed our stay!"
United States
Jennifer P.
The price is AED 343
AED 954 total
includes taxes & fees
11 Aug - 12 Aug
Endless Mountain Top Views from All The Way Up!
Exterior

11. 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, (32 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
The price is AED 476
AED 1,318 total
includes taxes & fees
12 Aug - 13 Aug
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Terrace/patio

12. Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (4 reviews)
"The place was great and we enjoyed our stay! Super comfy and cozy. Would definitely stay again!"
United States
Christopher H.
The price is AED 459
AED 1,067 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Lux Condo at Wintergreen Resort
Exterior

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

Pet-Friendly Retreat Walk to Slopes & Village!
Wintergreen Resort
10.0 out of 10, Exceptional, (1 review)
"A wonderful place to stay comfortable beds. The place was nice and clean "
United States
Denise P.
The price is AED 408
AED 1,072 total
includes taxes & fees
11 Aug - 12 Aug
Pet-Friendly Retreat Walk to Slopes & Village!
Exterior

14. 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 1,067 total
includes taxes & fees
24 Aug - 25 Aug
Mountain Retreat in Wintergreen!
Property grounds

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

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (40 reviews)
"Very clean and nicely supplied and decorated. Wonderful views from the living room! Planning on going back to this property again. "
United States
Charlie B.
The price is AED 500
AED 1,159 total
includes taxes & fees
17 Aug - 18 Aug
Luxury Condo in the Sky! Finest in Wintergreen!
Smart TV, fireplace

16. 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 460
AED 1,249 total
includes taxes & fees
11 Aug - 12 Aug
Bide-a-Wee- Hike the Trails! Close to the slopes!
Cabin, Private Bathroom (Bear Tracks Cottage) | Exterior

17. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is AED 672
AED 1,497 total
includes taxes & fees
11 Aug - 12 Aug
Bear Tracks Cottage
Exterior

18. Timbers Studio 46 with Wintergreen Advantage

Timbers Studio 46 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple...
United States
Madison D.
The price is AED 584
AED 989 total
includes taxes & fees
11 Aug - 12 Aug
Timbers Studio 46 with Wintergreen Advantage
Exterior

19. Mountain Inn Lodge 71 with Wintergreen Advantage

Mountain Inn Lodge 71 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, nice facilities.. polite staff "
United States
Rich C.
The price is AED 621
AED 1,088 total
includes taxes & fees
11 Aug - 12 Aug
Mountain Inn Lodge 71 with Wintergreen Advantage
Coffee/tea maker, fridge, microwave, oven

20. Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf

Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"Pet-friendly, very hospitable, had coffee and Brita filter for water, linens, paper towels, everything we needed. "
United States
Sarah L.
The price is AED 441
AED 1,114 total
includes taxes & fees
8 Sep - 9 Sep
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
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

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

10/10 Excellent
"Our stay at the property was amazing! Everything in the description was absolutely on point except for the views. They were so much better, but thats to be expected as those views are hard to describe! My family spent most of the time on the porch! The hosts were very helpful and very quick to respond! Overall a 5 star stay! We definitely recommed this condo and hope to come back here on our next vivst!"
Elliot P. 2-night trip
Posted 1 day ago
Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

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?

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 Theater Room, Fooseball, Firepit, Mountains! and Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!.

How many vacation rentals are there in Wintergreen?

Choose from 224 Expedia vacation rentals in Wintergreen for a memorable vacation.

What can I see and do in Wintergreen?

While exploring the area, visit family-friendly sights like War Fields, or get outside and enjoy nature at George Washington National Forest. 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.