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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Our top choices for Wintergreen vacation rentals

1. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (59 reviews)
"Nice resort"
United States
Diana J.
The price is ¥9,424
¥30,575 total
includes taxes & fees
Aug 26 - Aug 27
Where the Trail Ends

2. 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, (34 reviews)
"Everything was perfect! "
United States
Danielle B.
The price is ¥14,306
¥33,916 total
includes taxes & fees
Aug 26 - Aug 27
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

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, (159 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 ¥17,485
¥39,806 total
includes taxes & fees
Aug 26 - Aug 27
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

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 ¥18,573
¥43,349 total
includes taxes & fees
Aug 26 - Aug 27
Wintergreen Condo -Steps to Ski and restaurants

5. 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 ¥18,454
¥41,074 total
includes taxes & fees
Aug 26 - Aug 27
Escape to the Blue Ridge Mountains at Wine-tergreen!

6. 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 ¥16,451
¥49,714 total
includes taxes & fees
Aug 26 - Aug 27
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

7. First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (17 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
The price is ¥17,148
¥40,499 total
includes taxes & fees
Aug 31 - Sep 1
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

8. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is ¥29,088
¥64,796 total
includes taxes & fees
Sep 1 - Sep 2
Bear Tracks Cottage

9. First Floor Slope Side Wintergreen Condo – Ski In / Ski Out

First Floor Slope Side Wintergreen Condo – Ski In / Ski Out
Wintergreen Resort
10.0 out of 10, Exceptional, (9 reviews)
"Great little ski and ski out Property"
United States
Richard
The price is ¥18,050
¥39,753 total
includes taxes & fees
Aug 26 - Aug 27
First Floor Slope Side Wintergreen Condo – Ski In / Ski Out

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, (119 reviews)
"Gorgeous views! We spent most of our time out and about, but enjoyed our stay!"
United States
Jennifer P.
The price is ¥18,232
¥45,823 total
includes taxes & fees
Aug 27 - Aug 28
Endless Mountain Top Views from All The Way Up!

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, (56 reviews)
"Great place"
United States
Stephen M.
The price is ¥15,309
¥60,607 total
includes taxes & fees
Aug 26 - Aug 27
Spacious + Serene Mtn Top Escape, 4 En Suites

12. 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, (330 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 ¥17,485
¥41,949 total
includes taxes & fees
Sep 14 - Sep 15
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

13. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.8 out of 10, Exceptional, (47 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 ¥22,094
¥46,768 total
includes taxes & fees
Sep 8 - Sep 9
Panoramic Peak: Wintergreen Condo with Views

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, (32 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
The price is ¥20,600
¥57,049 total
includes taxes & fees
Aug 27 - Aug 28
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

15. Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (5 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 ¥19,869
¥46,164 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Lux Condo at Wintergreen Resort

16. 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 ¥19,869
¥46,164 total
includes taxes & fees
Aug 26 - Aug 27
Mountain Retreat in Wintergreen!

17. 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 ¥17,643
¥46,410 total
includes taxes & fees
Sep 8 - Sep 9
Pet-Friendly Retreat Walk to Slopes & Village!

18. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (14 reviews)
"Relaxing, scenic, quiet during the week, clean, modern, great communication with the host."
United States
Darlene
The price is ¥22,114
¥46,810 total
includes taxes & fees
Aug 30 - Aug 31
Mountain View Vista: Resort Condo w/ Views

19. Walk to Slopes, Village & Market. Pool, Dog-Friendly, Bonus Kids Room, Fireplace

Walk to Slopes, Village & Market. Pool, Dog-Friendly, Bonus Kids Room, Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (3 reviews)
"Condo was very clean, host was attentive. Location is great. Just a short walk to the market and the Edge. Great for a family of 5!"
United States
Valentina O.
The price is ¥17,882
¥53,641 total
includes taxes & fees
Aug 26 - Aug 27
Walk to Slopes, Village & Market. Pool, Dog-Friendly, Bonus Kids Room, Fireplace

20. 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, (122 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
The price is ¥29,406
¥56,229 total
includes taxes & fees
Aug 31 - Sep 1
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
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

Find out more about Wintergreen

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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 Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill.

How many vacation rentals are there in Wintergreen?

Choose from 227 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 Sherando Lake Recreation Area 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.