Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Wintergreen vacation rentals

A balcony with a table and chairs, offering a view of a mountainous landscape.

1. 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, (339 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
$216 nightly
The price is $242
Nov 17 - Nov 18
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
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 12 - Nov 13
Total with taxes and fees
Blackwood Chalet
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

3. 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.
$215 nightly
The price is $241
Nov 12 - Nov 13
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A two-story house with a front porch, a mailbox, and a wooden fence.

4. 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, (131 reviews)
"Awesome location. Cool set up and perfect for a couples getaway. The wood burning fireplace was a great thing."
United States
Paul
$205 nightly
The price is $230
Nov 12 - Nov 13
Total with taxes and fees
2 minutes from the shops and activities; Cozy 1 bedroom end unit.
A set of stone steps leading up to a house with a light-colored exterior.

5. 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.
$219 nightly
The price is $246
Nov 12 - Nov 13
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
A two-story house with a stone foundation, a large front porch, and a chimney.

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

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (128 reviews)
"Nice condo in a nice resort. House has everything you need and more."
United States
Thomas B.
$254 nightly
The price is $285
Nov 15 - Nov 16
Total with taxes and fees
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
A living room with a fireplace, a television mounted above it, a bookshelf, and a chair with a patterned cushion.

7. 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)
"Perfect condo for couple. Two bathrooms, big kitchen, big porch, big living area."
United States
Kathleen K.
$220 nightly
The price is $247
Nov 12 - Nov 13
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

8. 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
$324 nightly
The price is $363
Nov 12 - Nov 13
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.

9. Three Little Bears: Walk to Ski & Swim

Three Little Bears: Walk to Ski & Swim
Wintergreen Resort
9.6 out of 10, Exceptional, (14 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
$302 nightly
The price is $339
Nov 12 - Nov 13
Total with taxes and fees
Three Little Bears: Walk to Ski & Swim
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

10. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
10.0 out of 10, Exceptional, (41 reviews)
"It was a fine place for our family to stay during our staycation!"
United States
Alicia G.
$236 nightly
The price is $265
Nov 16 - Nov 17
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Private kitchen

11. "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.
$294 nightly
The price is $330
Nov 16 - Nov 17
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

12. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (50 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.
$274 nightly
The price is $308
Nov 12 - Nov 13
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

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

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (48 reviews)
"Views were amazing!"
United States
Sang Rea
$272 nightly
The price is $306
Nov 12 - Nov 13
Total with taxes and fees
Luxury Condo in the Sky! Finest in Wintergreen!
A two-story wooden cabin with a wooden deck and a small porch.

14. Walk to Market/Private community outdoor pool!

Walk to Market/Private community outdoor pool!
Wintergreen Resort
9.8 out of 10, Exceptional, (86 reviews)
"What a gem of a place! We had a wonderful long weekend get away as a family. The host communicated clearly and timely. We loved our stay here!"
United States
Christy P.
$215 nightly
The price is $241
Nov 12 - Nov 13
Total with taxes and fees
Walk to Market/Private community outdoor pool!
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.
$390 nightly
The price is $438
Nov 12 - Nov 13
Total with taxes and fees
Serenity Cabin-Woodland Retreat
A wooden deck with two Adirondack chairs facing a scenic view of a sunset over a mountainous landscape.

16. Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (125 reviews)
"Wow, they thought of everything you could need. This was one of the nicest places we have stayed. The price was amazing too. Definitely stay again"
United States
Sara C.
Endless Mountain Top Views from All The Way Up!
A two-story log cabin with a balcony, a staircase, and a snow-covered roof.

17. 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.
$242 nightly
The price is $272
Nov 16 - Nov 17
Total with taxes and fees
Pet-Friendly Retreat Walk to Slopes & Village!
A modern kitchen with white cabinetry, stainless steel appliances, a dining area with a wooden table and chairs, and a view through large windows.

18. 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.
$416 nightly
The price is $459
Nov 12 - Nov 13
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.

19. 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.
$323 nightly
The price is $363
Nov 12 - Nov 13
Total with taxes and fees
Your Ski-In and Ski-Out Wintergreen Escape
A swimming pool surrounded by lush greenery and a wooden cabin.

20. 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, (5 reviews)
"Condo was very clean, host was attentive. Location is great. Just a short walk to the market and the Edge. Great for a family of 5!"
United States
Valentina O.
$288 nightly
The price is $323
Nov 16 - Nov 17
Total with taxes and fees
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
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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Find vacation rentals that suit your style

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Top Wintergreen Hotel Reviews

A spacious living area with a wooden staircase, a dining table, and a sofa.
Blackwood Chalet

Blackwood Chalet

Blackwood Chalet
Nellysford

10/10 Excellent

Cleanliness and ease of check in
United States
Patrick
Reviewed September 13, 2026
Blackwood Chalet

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 $215 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.

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.

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