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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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.
$172 nightly
The price is $193
Sep 29 - Sep 30
Total with taxes and fees
Where the Trail Ends
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, (159 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 17 - Sep 18
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.
$189 nightly
The price is $212
Sep 17 - Sep 18
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.

4. 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.
$236 nightly
The price is $265
Sep 18 - Sep 19
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
A hotel room with a large bed, a desk, a chair, a lamp, and a view of the outdoor deck.

5. First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (17 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
$232 nightly
The price is $260
Sep 22 - Sep 23
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.

6. 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.
$261 nightly
The price is $293
Sep 17 - Sep 18
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
A mountainous landscape with dense green forests and a clear sky.

7. 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
$205 nightly
The price is $230
Sep 23 - Sep 24
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A wooden deck with a round table and chairs, overlooking a grassy area with trees.

8. 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
Sep 17 - Sep 18
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

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

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (57 reviews)
"Great spot and perfect for a family of 4-6. More than enough room. House was very clean. We will definitely come back!"
United States
Dawn
$337 nightly
The price is $379
Sep 17 - Sep 18
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
A hotel room with a bed, curtains, a window, and a view of the outside.

10. First Floor Slope Side Wintergreen Condo – Ski In / Ski Out

First Floor Slope Side Wintergreen Condo – Ski In / Ski Out
Wintergreen Resort
10.0 out of 10, Exceptional, (9 reviews)
"Great little ski and ski out Property"
United States
Richard
$232 nightly
The price is $249
Sep 17 - Sep 18
Total with taxes and fees
First Floor Slope Side Wintergreen Condo – Ski In / Ski Out
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

11. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
$245 nightly
The price is $275
Oct 4 - Oct 5
Total with taxes and fees
Three Little Bears
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, (35 reviews)
"Great stay for my family!"
United States
Joel M.
$227 nightly
The price is $255
Sep 17 - Sep 18
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A bedroom with a large bed, a dresser, and a ceiling fan. There are two windows providing a view of the outdoors.

13. 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
$254 nightly
The price is $285
Sep 28 - Sep 29
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views
A two-story house with a stone foundation, a large front porch, and a chimney.

14. 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, (122 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
$254 nightly
The price is $285
Sep 22 - Sep 23
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
A house with a covered patio, sliding glass doors, and a small outdoor seating area with chairs.

15. 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
Sep 17 - Sep 18
Total with taxes and fees
Mountain Retreat in Wintergreen!
A two-story log cabin with a balcony, a staircase, and a snow-covered roof.

16. 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.
$264 nightly
The price is $296
Sep 17 - Sep 18
Total with taxes and fees
Pet-Friendly Retreat Walk to Slopes & Village!

17. "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, (42 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
United States
Amy K.
$277 nightly
The price is $311
Sep 20 - Sep 21
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A cabin with a large window, surrounded by trees.

18. 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, (33 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
$319 nightly
The price is $358
Sep 17 - Sep 18
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A swimming pool surrounded by lush greenery and a wooden cabin.

19. 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.
$305 nightly
The price is $342
Sep 21 - Sep 22
Total with taxes and fees
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
A modern two-story house with a balcony, a deck, and a well-maintained garden.

20. 3BD & 3BA, Golf Access | Sleeps 12 | Pets OK

3BD & 3BA, Golf Access | Sleeps 12 | Pets OK
Wintergreen Resort
10.0 out of 10, Exceptional, (1 review)
"Wonderful and relaxing place to stay! Host was great to help us when needed!"
United States
Robbie H.
$368 nightly
The price is $421
Sep 17 - Sep 18
Total with taxes and fees
3BD & 3BA, Golf Access | Sleeps 12 | Pets OK
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

New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

10/10 Excellent
"The house was lovely -- lots of great indoor and outdoor space perfect for our group's getaway weekend. Hose was very communicative. House had everything we needed. Loved the open kitchen, dining and living room space. We enjoyed morning coffee and breakfast on the covered part of the deck and evenings in the hot tub. It rained the entire weekend so we weren't able to take advantage of the uncovered parts of the deck but would have loved to sit out there in the evenings. Would highly recommend and stay there again!"
Lisa L. 2-night trip
Posted 3 days ago
New Build! Log Cabin with Hot Tub in Wintergreen

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 $193 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?

Large and Luxurious Exec 5BR Chalet: Visitors give good reviews to this Wintergreen vacation home rental, which is located on a lake 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 and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Wintergreen are Wintergreen cabin, hot tub, sauna, walk to trails and Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK.

How many vacation rentals are there in Wintergreen?

Choose from 227 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.