A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

Wintergreen Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Wintergreen vacation rentals

A wooden deck with a round table and chairs, overlooking a grassy area with trees.

1. 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.
$229 nightly
The price is $257
Oct 4 - Oct 5
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
A garden with a variety of flowers and trees at dusk.

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, (161 reviews)
"It was a beautiful stay - we enjoyed the place and wished we could have stayed one more day to soak up the surroundings of the area more!"
United States
Michelle W.
$220 nightly
The price is $247
Nov 1 - Nov 2
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A room with a wooden floor, a table with two stools, and a view through large windows with blinds.

3. 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, (36 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
$199 nightly
The price is $223
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

4. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
$245 nightly
The price is $275
Nov 1 - Nov 2
Total with taxes and fees
Three Little Bears
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

5. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (38 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.
$249 nightly
The price is $280
Oct 2 - Oct 3
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
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, (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
$216 nightly
The price is $242
Oct 6 - Oct 7
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A two-story house with a stone foundation, a large front porch, and a chimney.

7. Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (124 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
$246 nightly
The price is $276
Oct 5 - Oct 6
Total with taxes and fees
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

8. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (37 reviews)
"Great stay for my family!"
United States
Joel M.
$227 nightly
The price is $255
Oct 4 - Oct 5
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A house with a covered patio, sliding glass doors, and a small outdoor seating area with chairs.

9. 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
Oct 4 - Oct 5
Total with taxes and fees
Mountain Retreat in Wintergreen!
A two-story wooden cabin with a wooden deck and a small porch.

10. Walk to Market/Private community outdoor pool!

Walk to Market/Private community outdoor pool!
Wintergreen Resort
9.8 out of 10, Exceptional, (85 reviews)
"Great location. Enjoyed our stay."
United States
Alice W.
$227 nightly
The price is $255
Oct 4 - Oct 5
Total with taxes and fees
Walk to Market/Private community outdoor pool!
Private kitchen

11. "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, (44 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
United States
Amy K.
$275 nightly
The price is $308
Oct 5 - Oct 6
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A house with a covered porch, two Adirondack chairs, and a welcome mat.

12. 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.
$286 nightly
The price is $290
Oct 12 - Oct 13
Total with taxes and fees
Cozy Lux Condo at Wintergreen Resort
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

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

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (60 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
$382 nightly
The price is $429
Oct 4 - Oct 5
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

14. Panoramic Peak

Panoramic Peak
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (1 review)
"The place was absolutely beautiful and spotless. The view was amazing. The only issue we had was when we asked where it was. We were told Nellysford and didn’t really understand that it was part of the Wintergreen resort so it was much further away from our actual destination. But the place was really amazing. We would stay there again."
United States
Carrie
$243 nightly
The price is $273
Oct 12 - Oct 13
Total with taxes and fees
Panoramic Peak
A cabin with a large window, surrounded by trees.

15. 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, (35 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
$339 nightly
The price is $381
Oct 7 - Oct 8
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A wooden deck with two Adirondack chairs facing a scenic view of a sunset over a mountainous landscape.

16. 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, (121 reviews)
"Gorgeous views! We spent most of our time out and about, but enjoyed our stay!"
United States
Jennifer P.
$293 nightly
The price is $329
Oct 4 - Oct 5
Total with taxes and fees
Endless Mountain Top Views from All The Way Up!
A loft bedroom with a sloped ceiling, a bed with plaid bedding, a dark dresser, and a view of the outdoors through a window.

17. 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.
$388 nightly
The price is $436
Oct 4 - Oct 5
Total with taxes and fees
Serenity Cabin-Woodland Retreat
An aerial view of a residential area with multiple houses surrounded by dense forest, featuring a central building with a prominent roof and a well-lit driveway.

18. Mountain Inn Lodge 77 with Wintergreen Advantage

Mountain Inn Lodge 77 with Wintergreen Advantage
Wintergreen
8.0 out of 10, Very good, (1 review)
"The stairs inside the property makes hard to lug the suitcases around little hard."
United States
Bhaskar
$225 nightly
The price is $253
Nov 1 - Nov 2
Total with taxes and fees
Mountain Inn Lodge 77 with Wintergreen Advantage
Exterior

19. 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.
$201 nightly
The price is $226
Nov 1 - Nov 2
Total with taxes and fees
Timbers Studio 46 with Wintergreen Advantage
An aerial view of a large estate with multiple buildings surrounded by dense forest and mountains in the background.

20. Mountain Inn Studio 93 with Wintergreen Advantage

Mountain Inn Studio 93 with Wintergreen Advantage
Wintergreen
$212 nightly
The price is $238
Nov 1 - Nov 2
Total with taxes and fees
Mountain Inn Studio 93 with Wintergreen Advantage
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

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants

10/10 Excellent
"This well-equipped condo was central to the market and restaurants. We enjoyed the fireplace and the deck."
Lynne F. 4-night trip
Posted 2 days ago
Wintergreen Condo -Steps to Ski and restaurants

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 $242 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?

Wintergreen cabin, hot tub, sauna, walk to trails: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 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 Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 and Remodeled 3BR/2BA Ski Chalet off Tyro Slope.

How many vacation rentals are there in Wintergreen?

Choose from 232 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.