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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Wintergreen vacation rentals

A room with a wooden floor, a table with two stools, and a view through large windows with blinds.

1. 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.
$189 nightly
The price is $212
Oct 12 - Oct 13
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
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.
$222 nightly
The price is $249
Nov 1 - Nov 2
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

3. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
$260 nightly
The price is $292
Oct 12 - Oct 13
Total with taxes and fees
Three Little Bears
A wooden deck with a round table and chairs, overlooking a grassy area with trees.

4. Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.6 out of 10, Exceptional, (130 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
$230 nightly
The price is $258
Oct 12 - Oct 13
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
A mountainous landscape with dense green forests and a clear sky.

5. 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, (335 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
$227 nightly
The price is $254
Oct 25 - Oct 26
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

6. 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.
$226 nightly
The price is $254
Oct 12 - Oct 13
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

7. 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 12 - Oct 13
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Private kitchen

8. "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.
$277 nightly
The price is $311
Oct 12 - Oct 13
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

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

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (45 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.
$280 nightly
The price is $315
Oct 12 - Oct 13
Total with taxes and fees
Luxury Condo in the Sky! Finest in Wintergreen!
A covered outdoor deck with a round table and chairs, overlooking a lush landscape.

10. Overlook 180 degree views w/Peloton!

Overlook 180 degree views w/Peloton!
Wintergreen Resort
9.4 out of 10, Exceptional, (3 reviews)
"Excellent stay. Thank you!"
United States
Kimberly B.
$279 nightly
The price is $319
Oct 13 - Oct 14
Total with taxes and fees
Overlook 180 degree views w/Peloton!
Exterior

11. 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.
$203 nightly
The price is $228
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.

12. Mountain Inn Studio 93 with Wintergreen Advantage

Mountain Inn Studio 93 with Wintergreen Advantage
Wintergreen
$214 nightly
The price is $240
Nov 1 - Nov 2
Total with taxes and fees
Mountain Inn Studio 93 with Wintergreen Advantage
A balcony with a table and chairs, overlooking a lush landscape.

13. 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
$229 nightly
The price is $257
Nov 2 - Nov 3
Total with taxes and fees
Panoramic Peak
A two-story house with a stone foundation, a large front porch, and a chimney.

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

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (125 reviews)
"Nice condo in a nice resort. House has everything you need and more."
United States
Thomas B.
$292 nightly
The price is $327
Oct 12 - Oct 13
Total with taxes and fees
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
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.

15. 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
$226 nightly
The price is $254
Nov 1 - Nov 2
Total with taxes and fees
Mountain Inn Lodge 77 with Wintergreen Advantage
Exterior

16. 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.
$226 nightly
The price is $254
Nov 1 - Nov 2
Total with taxes and fees
Mountain Inn Lodge 71 with Wintergreen Advantage
A dining area with a wooden table, chairs, and a view of the kitchen.

17. Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails

Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
Wintergreen Resort
10.0 out of 10, Exceptional, (6 reviews)
$291 nightly
The price is $327
Nov 2 - Nov 3
Total with taxes and fees
Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
A two-story log cabin with a balcony, a staircase, and a snow-covered roof.

18. 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.
$257 nightly
The price is $289
Oct 12 - Oct 13
Total with taxes and fees
Pet-Friendly Retreat Walk to Slopes & Village!
Exterior

19. Diamond Hill Studio 09 with Wintergreen Advantage

Diamond Hill Studio 09 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (3 reviews)
"Great location and cozy condo! "
United States
Molly M.
$240 nightly
The price is $269
Nov 1 - Nov 2
Total with taxes and fees
Diamond Hill Studio 09 with Wintergreen Advantage
A modern kitchen with white cabinetry, a black stove, and a dining area with a chandelier.

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.
$257 nightly
The price is $289
Oct 12 - Oct 13
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

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

10/10 Excellent
"Beautiful place, has everything you can imagine, the view is also amazing, 100% recommended."
Monica C. 3-night trip
Posted 3 days ago
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

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 $212 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.