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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Our top choices for Wintergreen vacation rentals

1. 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.
The price is CA $157
CA $348 total
includes taxes & fees
Nov 16 - Nov 17
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

2. 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
The price is CA $141
CA $324 total
includes taxes & fees
Nov 16 - Nov 17
2 minutes from the shops and activities; Cozy 1 bedroom end unit.

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.
The price is CA $141
CA $340 total
includes taxes & fees
Nov 16 - Nov 17
Updated! Cozy and clean two bedroom condo.

4. 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.
The price is CA $166
CA $351 total
includes taxes & fees
Nov 16 - Nov 17
Escape to the Blue Ridge Mountains at Wine-tergreen!

5. 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, (340 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is CA $134
CA $341 total
includes taxes & fees
Nov 16 - Nov 17
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

6. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
The price is CA $186
CA $449 total
includes taxes & fees
Nov 16 - Nov 17
Three Little Bears

7. 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.
The price is CA $141
CA $340 total
includes taxes & fees
Nov 16 - Nov 17
Walk to Market/Private community outdoor pool!

8. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (50 reviews)
"Amazing views and beautiful sunsets. "
United States
Erica T.
The price is CA $235
CA $443 total
includes taxes & fees
Nov 16 - Nov 17
Panoramic Peak: Wintergreen Condo with Views

9. Mountain Inn Studio 96 with Wintergreen Advantage

Mountain Inn Studio 96 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"A wonderful condo at Wintergreen! It was great to snowboard the whole day and the next day. This was a lovely and clean place to rest. "
United States
Lana
The price is CA $184
CA $304 total
includes taxes & fees
Nov 16 - Nov 17
Mountain Inn Studio 96 with Wintergreen Advantage

10. Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
Wintergreen Resort
9.8 out of 10, Exceptional, (151 reviews)
"Great place, super clean, and wonderful location on the mountain!"
United States
Frank A.
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

11. 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.
The price is CA $184
CA $404 total
includes taxes & fees
Nov 17 - Nov 18
Wintergreen Condo -Steps to Ski and restaurants

12. 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
The price is CA $144
CA $523 total
includes taxes & fees
Nov 16 - Nov 17
Spacious + Serene Mtn Top Escape, 4 En Suites

13. 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.
The price is CA $198
CA $395 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace

14. "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.
The price is CA $175
CA $467 total
includes taxes & fees
Nov 16 - Nov 17
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

15. Timbers Studio 46 with Wintergreen Advantage

Timbers Studio 46 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple...
United States
Madison D.
The price is CA $184
CA $304 total
includes taxes & fees
Nov 16 - Nov 17
Timbers Studio 46 with Wintergreen Advantage

16. Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
The price is CA $252
CA $427 total
includes taxes & fees
Nov 16 - Nov 17
Mountain View Vista

17. 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
The price is CA $198
CA $339 total
includes taxes & fees
Nov 16 - Nov 17
Mountain Inn Lodge 77 with Wintergreen Advantage

18. Mountain Inn Lodge 78 with Wintergreen Advantage

Mountain Inn Lodge 78 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"Had so much fun! Perfect stay!"
United States
Megan O.
The price is CA $198
CA $339 total
includes taxes & fees
Nov 16 - Nov 17
Mountain Inn Lodge 78 with Wintergreen Advantage

19. 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
The price is CA $203
CA $439 total
includes taxes & fees
Nov 16 - Nov 17
Luxury Condo in the Sky! Finest in Wintergreen!

20. Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails

Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
Wintergreen Resort
10.0 out of 10, Exceptional, (9 reviews)
The price is CA $190
CA $453 total
includes taxes & fees
Nov 16 - Nov 17
Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
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

Find out more about Wintergreen

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Wintergreen. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.