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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
Oct 20 - Oct 21
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
$412 nightly
The price is $462
Oct 20 - Oct 21
Total with taxes and fees
Blackwood Chalet
Private kitchen

3. "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.
$276 nightly
The price is $309
Oct 20 - Oct 21
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
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, (337 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
$224 nightly
The price is $251
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.

5. 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 20 - Oct 21
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A two-story wooden cabin with a wooden deck and a small porch.

6. Walk to Market/Private community outdoor pool!

Walk to Market/Private community outdoor pool!
Wintergreen Resort
9.8 out of 10, Exceptional, (85 reviews)
"Very nice, looks like a new home, comfortable. But as it is a mountain resort watch for bears, we had one walk right near the car, we were glad we were inside the car at that time."
United States
Robyn M.
$225 nightly
The price is $253
Oct 20 - Oct 21
Total with taxes and fees
Walk to Market/Private community outdoor pool!
A staircase with a wooden handrail and a carpeted landing.

7. Three Little Bears: Walk to Ski & Swim

Three Little Bears: Walk to Ski & Swim
Wintergreen Resort
9.4 out of 10, Exceptional, (12 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
$317 nightly
The price is $356
Oct 20 - Oct 21
Total with taxes and fees
Three Little Bears: Walk to Ski & Swim
A garden with a variety of flowers and trees at dusk.

8. 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.
$216 nightly
The price is $243
Nov 1 - Nov 2
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A two-story house with a stone foundation, a large front porch, and a chimney.

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

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (126 reviews)
"Nice condo in a nice resort. House has everything you need and more."
United States
Thomas B.
$293 nightly
The price is $328
Oct 22 - Oct 23
Total with taxes and fees
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.

10. 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 modern living room with a grey sofa set, a coffee table, and a fireplace.

11. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (16 reviews)
"A beautiful property with spectacular mountains view, sunrise and many stars at night. Really enjoyed the stay."
United States
Harumi
$300 nightly
The price is $337
Oct 20 - Oct 21
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views
A bedroom with a four-poster bed, a television on a wooden cabinet, and a view of greenery through a window.

12. 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.
$385 nightly
The price is $433
Oct 20 - Oct 21
Total with taxes and fees
Serenity Cabin-Woodland Retreat
A two-story log cabin with a balcony, a staircase, and a snow-covered roof.

13. 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.
$261 nightly
The price is $293
Oct 20 - Oct 21
Total with taxes and fees
Pet-Friendly Retreat Walk to Slopes & Village!
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

14. 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
$416 nightly
The price is $467
Oct 25 - Oct 26
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
A swimming pool surrounded by lush greenery and a wooden cabin.

15. 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.
$316 nightly
The price is $355
Nov 9 - Nov 10
Total with taxes and fees
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
A cabin with a large window, surrounded by trees.

16. 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.
$334 nightly
The price is $375
Nov 16 - Nov 17
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A modern kitchen with white cabinetry, stainless steel appliances, a dining area with a wooden table and chairs, and a view through large windows.

17. Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (40 reviews)
"Very organized information and amazing communication from host ahead of arrival; the view and location are amazing, and the accommodations were comfortable and made for an easy and fun adventure! Will definitely stay here again. "
United States
Blayre G.
$368 nightly
The price is $406
Oct 25 - Oct 26
Total with taxes and fees
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
A modern kitchen with white cabinetry, a large island with bar stools, stainless steel appliances, and a chandelier.

18. Your Ski-In and Ski-Out Wintergreen Escape

Your Ski-In and Ski-Out Wintergreen Escape
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place!"
United States
Chris C.
$364 nightly
The price is $409
Nov 3 - Nov 4
Total with taxes and fees
Your Ski-In and Ski-Out Wintergreen Escape
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.

19. 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
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.
$290 nightly
The price is $326
Nov 16 - Nov 17
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

Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

10/10 Excellent
"We were so fortunate to find this spectacular gem! The breathtaking views that pictures just cannot do justice for were amazing! The unit was so well stocked with all the essentials and one of the cleanest places we have stayed. Check-in and check-out were clear and simple. We can’t wait to book again. Thank you for sharing your piece of mountain with us. We loved it."
Traci A. 3-night trip
Posted 1 day ago
Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

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.