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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Wintergreen vacation rentals

Property grounds

1. 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
$220 nightly
The price is $247
Sep 9 - Sep 10
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Living area

2. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (60 reviews)
"Nice resort"
United States
Diana J.
$159 nightly
The price is $178
Sep 9 - Sep 10
Total with taxes and fees
Where the Trail Ends
Terrace/patio

3. 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.
$236 nightly
The price is $265
Sep 9 - Sep 10
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Apartment, Private Bathroom (Three Little Bears ) | Exterior

4. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
$245 nightly
The price is $275
Oct 5 - Oct 6
Total with taxes and fees
Three Little Bears
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, (34 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
$188 nightly
The price is $211
Sep 9 - Sep 10
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
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, (42 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
United States
Amy K.
$275 nightly
The price is $308
Sep 9 - Sep 10
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
Outdoor dining

7. 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.
$230 nightly
The price is $258
Sep 9 - Sep 10
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
Living area

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

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (57 reviews)
"Great spot and perfect for a family of 4-6. More than enough room. House was very clean. We will definitely come back!"
United States
Dawn
$334 nightly
The price is $375
Sep 9 - Sep 10
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
Room

9. 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.
$219 nightly
The price is $246
Sep 9 - Sep 10
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Room

10. 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
$230 nightly
The price is $247
Sep 9 - Sep 10
Total with taxes and fees
First Floor Slope Side Wintergreen Condo – Ski In / Ski Out
A mountainous landscape with dense green forests and a clear sky.

11. 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
$223 nightly
The price is $250
Sep 14 - Sep 15
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Property grounds

12. 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.
$259 nightly
The price is $291
Sep 9 - Sep 10
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
Dining

13. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (35 reviews)
"Everything was great! Very accommodating host and lovely place!"
United States
Jason S.
$225 nightly
The price is $253
Sep 9 - Sep 10
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
Cabin, Private Bathroom (Bear Tracks Cottage) | Exterior

14. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
$363 nightly
The price is $408
Sep 9 - Sep 10
Total with taxes and fees
Bear Tracks Cottage
Exterior

15. 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.
$290 nightly
The price is $325
Sep 9 - Sep 10
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Exterior

16. 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.
$256 nightly
The price is $287
Sep 10 - Sep 11
Total with taxes and fees
Pet-Friendly Retreat Walk to Slopes & Village!
Exterior

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.
$282 nightly
The price is $286
Sep 9 - Sep 10
Total with taxes and fees
Mountain Retreat in Wintergreen!
Exterior

18. 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.
$336 nightly
The price is $377
Sep 17 - Sep 18
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Property grounds

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

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (43 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.
$278 nightly
The price is $312
Sep 9 - Sep 10
Total with taxes and fees
Luxury Condo in the Sky! Finest in Wintergreen!
Pool

20. 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.
$305 nightly
The price is $342
Sep 9 - Sep 10
Total with taxes and fees
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
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

Newly Built Designer Home in Wintergreen

Newly Built Designer Home in Wintergreen

10/10 Excellent
"Modern interior with all the extras. Beds were comfortable and linens were nice. Kitchen is well appointed. Lots of appropriate storage. We will return next summet"
Gail C. 3-night trip
Posted 3 days ago
Newly Built Designer Home in Wintergreen

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 $247 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?

Large and Luxurious Exec 5BR Chalet: Visitors give good reviews to this Wintergreen vacation home rental, which is located on a lake 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 and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Wintergreen are Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK and Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope.

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 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.