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 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 living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.

1. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (60 reviews)
"Nice resort"
United States
Diana J.
$191 nightly
The price is $214
Oct 5 - Oct 6
Total with taxes and fees
Where the Trail Ends
A wooden deck with a round table and chairs, overlooking a grassy area with trees.

2. 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 30 - Oct 1
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.

3. 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)
"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
$222 nightly
The price is $249
Sep 30 - Oct 1
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.

4. 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
Sep 30 - Oct 1
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
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, (37 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
Sep 30 - Oct 1
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
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, (44 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
United States
Amy K.
$277 nightly
The price is $311
Sep 30 - Oct 1
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
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.
$247 nightly
The price is $277
Sep 30 - Oct 1
Total with taxes and fees
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
A two-story wooden cabin with a wooden deck and a small porch.

8. 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.
$226 nightly
The price is $254
Sep 30 - Oct 1
Total with taxes and fees
Walk to Market/Private community outdoor pool!
A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.

9. 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.
$260 nightly
The price is $292
Sep 30 - Oct 1
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
A mountainous landscape with dense green forests and a clear sky.

10. 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
Sep 30 - Oct 1
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

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, (60 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
$389 nightly
The price is $437
Oct 4 - Oct 5
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

12. 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
Sep 30 - Oct 1
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

13. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
$245 nightly
The price is $275
Oct 1 - Oct 2
Total with taxes and fees
Three Little Bears
A cabin with a large window, surrounded by trees.

14. 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.
$340 nightly
The price is $382
Oct 7 - Oct 8
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A modern living room with a grey sofa set, a coffee table, and a fireplace.

15. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (15 reviews)
"Relaxing, scenic, quiet during the week, clean, modern, great communication with the host."
United States
Darlene
$260 nightly
The price is $292
Sep 30 - Oct 1
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views
A swimming pool surrounded by lush greenery and a wooden cabin.

16. 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.
$360 nightly
The price is $404
Sep 30 - Oct 1
Total with taxes and fees
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
A house with a covered patio, sliding glass doors, and a small outdoor seating area with chairs.

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.
$284 nightly
The price is $288
Sep 30 - Oct 1
Total with taxes and fees
Mountain Retreat in Wintergreen!
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.
$270 nightly
The price is $303
Oct 12 - Oct 13
Total with taxes and fees
Pet-Friendly Retreat Walk to Slopes & Village!
A cozy living room with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.

19. 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.
$347 nightly
The price is $398
Oct 4 - Oct 5
Total with taxes and fees
Bide-a-Wee- Hike the Trails! Close to the slopes!
A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

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, (44 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
Sep 30 - Oct 1
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

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

10/10 Excellent
"Amazing property and owners"
Francis B. 1-night trip
Posted 19 hours ago
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

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 $214 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.