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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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.
$182 nightly
The price is $204
Aug 18 - Aug 19
Total with taxes and fees
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
$223 nightly
The price is $250
Aug 9 - Aug 10
Total with taxes and fees
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.
$278 nightly
The price is $312
Aug 9 - Aug 10
Total with taxes and fees
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.
$238 nightly
The price is $267
Aug 18 - Aug 19
Total with taxes and fees
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.
$189 nightly
The price is $212
Aug 10 - Aug 11
Total with taxes and fees
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.
$224 nightly
The price is $251
Aug 18 - Aug 19
Total with taxes and fees
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
$229 nightly
The price is $257
Aug 9 - Aug 10
Total with taxes and fees
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.
$230 nightly
The price is $258
Aug 9 - Aug 10
Total with taxes and fees
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, (120 reviews)
"Great location"
United States
Chrissy R.
$263 nightly
The price is $295
Aug 10 - Aug 11
Total with taxes and fees
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.
$235 nightly
The price is $264
Aug 10 - Aug 11
Total with taxes and fees
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.
$318 nightly
The price is $357
Aug 27 - Aug 28
Total with taxes and fees
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.
$286 nightly
The price is $290
Aug 16 - Aug 17
Total with taxes and fees
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.
$259 nightly
The price is $291
Aug 9 - Aug 10
Total with taxes and fees
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.
$285 nightly
The price is $289
Aug 9 - Aug 10
Total with taxes and fees
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, (39 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.
$281 nightly
The price is $316
Aug 9 - Aug 10
Total with taxes and fees
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.
$312 nightly
The price is $359
Aug 31 - Sep 1
Total with taxes and fees
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
$363 nightly
The price is $408
Aug 31 - Sep 1
Total with taxes and fees
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.
$241 nightly
The price is $270
Aug 9 - Aug 10
Total with taxes and fees
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.
$265 nightly
The price is $297
Aug 9 - Aug 10
Total with taxes and fees
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.
$261 nightly
The price is $293
Sep 1 - Sep 2
Total with taxes and fees
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

View from the Top

View from the Top

10/10 Excellent
"Peace, Quiet, a Beautiful View, Clean Air, Clean Water. Unit was very well equipped. And the support was excellent."
John B. 7-night trip
Posted 1 day ago
View from the Top

Find out more about Wintergreen

Everything you need to know about Wintergreen vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wintergreen vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wintergreen vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wintergreen. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wintergreen in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $204 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wintergreen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wintergreen vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wintergreen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.