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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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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

Our top choices for Wintergreen vacation rentals

Exterior

1. 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)
"Great location"
United States
Chrissy R.
$237 nightly
The price is $266
Aug 13 - Aug 14
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Cabin, Private Bathroom (Blackwood Chalet) | Lounge

2. Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (5 reviews)
"Love the area"
United States
Toni
$373 nightly
The price is $419
Aug 16 - Aug 17
Total with taxes and fees
Blackwood Chalet
Exterior

3. Overlook 08 with Wintergreen Advantage

Overlook 08 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"Great view, wonderful property, and extremely helpful staff (we experienced a vehicle crisis)."
United States
Jason
$452 nightly
The price is $507
Aug 14 - Aug 15
Total with taxes and fees
Overlook 08 with Wintergreen Advantage
Property grounds

4. 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.
$269 nightly
The price is $303
Aug 23 - Aug 24
Total with taxes and fees
Endless Mountain Top Views from All The Way Up!
Exterior

5. 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.
$319 nightly
The price is $358
Aug 16 - Aug 17
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Smart TV, video games

6. Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
9.8 out of 10, Exceptional, (17 reviews)
"Wonderful stay with great communication with the host "
United States
Annamarie P.
$390 nightly
The price is $438
Aug 16 - Aug 17
Total with taxes and fees
Serenity Cabin-Woodland Retreat
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, (128 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
$230 nightly
The price is $258
Aug 16 - Aug 17
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
Terrace/patio

8. 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.
$240 nightly
The price is $269
Aug 18 - Aug 19
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Coffee/tea maker, fridge, microwave, oven

9. Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (39 reviews)
"We had an incredible stay this past week. The condo "
United States
Holly M.
$371 nightly
The price is $410
Aug 16 - Aug 17
Total with taxes and fees
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Exterior

10. Overlook 26 with Wintergreen Advantage

Overlook 26 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
$452 nightly
The price is $507
Aug 14 - Aug 15
Total with taxes and fees
Overlook 26 with Wintergreen Advantage
Smart TV, fireplace, books

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.
$394 nightly
The price is $442
Aug 15 - Aug 16
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
Interior

12. Lofty Pursuits: Spectacular View + EV Charger

Lofty Pursuits: Spectacular View + EV Charger
Treeloft
10.0 out of 10, Exceptional, (24 reviews)
"Great place to stay"
United States
David T.
$393 nightly
The price is $420
Aug 13 - Aug 14
Total with taxes and fees
Lofty Pursuits: Spectacular View + EV Charger
Exterior

13. Cliffs 27 with Wintergreen Advantage

Cliffs 27 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"The property has amazing views overlooking wintergreen resort! Very spacious Livingroom/ Dining/ kitchen area compared to most condos at the resort. Only downside was the dull kitchen knives but that didn't take away from the amazing sunrise views!Thank you for the great stay!"
United States
James M.
$452 nightly
The price is $507
Aug 13 - Aug 14
Total with taxes and fees
Cliffs 27 with Wintergreen Advantage
Property grounds

14. 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
$221 nightly
The price is $248
Aug 13 - Aug 14
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Exterior

15. Stoneridge Woods 05 with Wintergreen Advantage

Stoneridge Woods 05 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"Loved the house. The layout was great and worked great for our family."
United States
Torry M.
$414 nightly
The price is $465
Aug 14 - Aug 15
Total with taxes and fees
Stoneridge Woods 05 with Wintergreen Advantage
Coffee/tea maker, fridge, microwave, oven

16. Luxury Mountain Retreat I Views I Ski in, Ski out I 3 Beds, 2 Baths - Sleeps 10

Luxury Mountain Retreat I Views I Ski in, Ski out I 3 Beds, 2 Baths - Sleeps 10
Pedlars Edge
10.0 out of 10, Exceptional, (6 reviews)
"Great location and nice home!"
United States
Hesham A.
$680 nightly
The price is $764
Aug 13 - Aug 14
Total with taxes and fees
Luxury Mountain Retreat I Views I Ski in, Ski out I 3 Beds, 2 Baths - Sleeps 10
Smart TV, fireplace, table tennis, books

17. 4 BR cabin mins to trails & breweries pets welcome

4 BR cabin mins to trails & breweries pets welcome
Chestnut Springs
9.6 out of 10, Exceptional, (35 reviews)
"We really enjoyed our stay in Wintergreen! The location was great and the view was incredible. The house was spotless and we loved that there was a full kitchen. We recommend to others! "
United States
Laura J.
$529 nightly
The price is $594
Aug 13 - Aug 14
Total with taxes and fees
4 BR cabin mins to trails & breweries pets welcome
Dining

18. Bear Tracks Cottage: New Hot Tub + Fire Pit

Bear Tracks Cottage: New Hot Tub + Fire Pit
Nellysford
10.0 out of 10, Exceptional, (36 reviews)
"We loved the location! This cabin has everything you need for the perfect mountain getaway."
United States
Amanda
$413 nightly
The price is $464
Sep 1 - Sep 2
Total with taxes and fees
Bear Tracks Cottage: New Hot Tub + Fire Pit
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 13 - Aug 14
Total with taxes and fees
Mountain Inn Lodge 71 with Wintergreen Advantage
Property grounds

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, (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.
$281 nightly
The price is $316
Aug 17 - Aug 18
Total with taxes and fees
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

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

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 $199 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.