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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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
9.6 out of 10, Exceptional, (132 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
$230 nightly
The price is $258
Nov 1 - Nov 2
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
A spacious living area with a wooden staircase, a dining table, and a sofa.

2. Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (6 reviews)
"Cleanliness and ease of check in"
United States
Patrick
$376 nightly
The price is $423
Nov 2 - Nov 3
Total with taxes and fees
Blackwood Chalet
A two-story house with a front porch, a mailbox, and a wooden fence.

3. 2 minutes from the shops and activities; Cozy 1 bedroom end unit.

2 minutes from the shops and activities; Cozy 1 bedroom end unit.
Wintergreen
9.4 out of 10, Exceptional, (129 reviews)
"Clean property that was well equipped, and easy check in."
United States
Joseph Blaine
$205 nightly
The price is $230
Nov 1 - Nov 2
Total with taxes and fees
2 minutes from the shops and activities; Cozy 1 bedroom end unit.
A mountainous landscape with dense green forests and a clear sky.

4. 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, (338 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
$217 nightly
The price is $243
Nov 3 - Nov 4
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A garden with a variety of flowers and trees at dusk.

5. 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, (163 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 2 - Nov 3
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
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, (38 reviews)
"Great stay for my family!"
United States
Joel M.
$225 nightly
The price is $253
Nov 1 - Nov 2
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

7. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (49 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.
$289 nightly
The price is $325
Nov 16 - Nov 17
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
A two-story house with a stone foundation, a large front porch, and a chimney.

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

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (127 reviews)
"Nice condo in a nice resort. House has everything you need and more."
United States
Thomas B.
$290 nightly
The price is $325
Nov 2 - Nov 3
Total with taxes and fees
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

9. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (39 reviews)
"It was a fine place for our family to stay during our staycation!"
United States
Alicia G.
$270 nightly
The price is $303
Nov 3 - Nov 4
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Private kitchen

10. "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.
$270 nightly
The price is $303
Nov 2 - Nov 3
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
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, (61 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
$339 nightly
The price is $381
Nov 1 - Nov 2
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

12. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
$280 nightly
The price is $315
Nov 3 - Nov 4
Total with taxes and fees
Three Little Bears
A two-story wooden cabin with a wooden deck and a small porch.

13. 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.
$225 nightly
The price is $253
Nov 1 - Nov 2
Total with taxes and fees
Walk to Market/Private community outdoor pool!
A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

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

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (47 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
Nov 5 - Nov 6
Total with taxes and fees
Luxury Condo in the Sky! Finest in Wintergreen!
A spacious cabin interior with a large living area, a deck, and a 'PRODUCE' sign on the wall.

15. Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
9.8 out of 10, Exceptional, (18 reviews)
"Wonderful stay with great communication with the host "
United States
Annamarie P.
$412 nightly
The price is $463
Nov 3 - Nov 4
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.

16. 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 3 - Nov 4
Total with taxes and fees
Mountain Inn Lodge 77 with Wintergreen Advantage
A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.

17. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (18 reviews)
"A beautiful property with spectacular mountains view, sunrise and many stars at night. Really enjoyed the stay."
United States
Harumi
$303 nightly
The price is $341
Nov 3 - Nov 4
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views
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.
$258 nightly
The price is $289
Nov 9 - Nov 10
Total with taxes and fees
Pet-Friendly Retreat Walk to Slopes & Village!
A cabin with a large window, surrounded by trees.

19. 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, (37 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
$332 nightly
The price is $373
Nov 4 - Nov 5
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Exterior

20. 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.
$238 nightly
The price is $267
Nov 1 - Nov 2
Total with taxes and fees
Diamond Hill Studio 09 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

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

10/10 Excellent
"Brilliantly decorated and had the feel of a European apartment. From the moment we walked in, we were blown away by the attention to detail, thoughtful design, and cozy, historic charm. The decor effortlessly blended classic elegance with modern comfort, making it feel like a curated retreat rather than just a rental. Well done, Amy!"
matthew r. 2-night trip
Posted 16 hours ago
Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

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 $243 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.