A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

Wintergreen Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Wintergreen vacation rentals

Fireplace

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (57 reviews)
"Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go!"
United States
Meredith T.
The price is SAR 288
SAR 801 total
includes taxes & fees
21 Jul - 22 Jul
Where the Trail Ends
Exterior

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, (119 reviews)
"Great location"
United States
Chrissy R.
The price is SAR 615
SAR 1,180 total
includes taxes & fees
19 Jul - 20 Jul
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Property grounds

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, (156 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 SAR 413
SAR 940 total
includes taxes & fees
22 Jul - 23 Jul
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (10 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
The price is SAR 357
SAR 1,053 total
includes taxes & fees
19 Jul - 20 Jul
Laurelwood Hollow: Walk to Ski & Swim
Property grounds

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, (111 reviews)
"Nice place!"
United States
Gregory G.
The price is SAR 413
SAR 1,058 total
includes taxes & fees
20 Jul - 21 Jul
Endless Mountain Top Views from All The Way Up!

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, (325 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is SAR 436
SAR 1,017 total
includes taxes & fees
27 Jul - 28 Jul
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
TV, fireplace

Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (14 reviews)
"This was a wonderful stay, the unit was clean, comfortable, and the property managers were immediate to respond with any questions. We will definitely stay here again. The 2nd full bathroom was a plus!And the view, was breathtaking any time of day!Our stay was quiet and peaceful, just what was needed!!"
United States
Judy M.
Mountain View Vista: Resort Condo w/ Views
Smart TV, fireplace, books

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (56 reviews)
"Great place"
United States
Stephen M.
The price is SAR 387
SAR 1,455 total
includes taxes & fees
20 Jul - 21 Jul
Spacious + Serene Mtn Top Escape, 4 En Suites
Cabin, Private Bathroom (Bear Tracks Cottage) | Exterior

Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is SAR 706
SAR 1,552 total
includes taxes & fees
2 Aug - 3 Aug
Bear Tracks Cottage
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (35 reviews)
"Condo was as advertised, perfect for a quick trip up to Wintergreen!"
United States
Jason L.
The price is SAR 428
SAR 983 total
includes taxes & fees
21 Jul - 22 Jul
Wintergreen Condo -Steps to Ski and restaurants
Interior

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, (31 reviews)
"Everything was perfect! "
United States
Danielle B.
The price is SAR 376
SAR 848 total
includes taxes & fees
22 Jul - 23 Jul
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Exterior

Pet-Friendly Retreat Walk to Slopes & Village!

Pet-Friendly Retreat Walk to Slopes & Village!
Wintergreen Resort
10.0 out of 10, Exceptional, (1 review)
"A wonderful place to stay comfortable beds. The place was nice and clean "
United States
Denise P.
Pet-Friendly Retreat Walk to Slopes & Village!
Outdoor dining

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, (128 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is SAR 436
SAR 966 total
includes taxes & fees
20 Jul - 21 Jul
Escape to the Blue Ridge Mountains at Wine-tergreen!
Exterior

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.
The price is SAR 582
SAR 1,195 total
includes taxes & fees
15 Aug - 16 Aug
Mountain Retreat in Wintergreen!
Smart TV

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
9.8 out of 10, Exceptional, (17 reviews)
"Very nice cabin, beautiful decorations. "
United States
Gabrielle M.
Serenity Cabin-Woodland Retreat
Coffee/tea maker, fridge, microwave, oven

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Wintergreen Resort
10.0 out of 10, Exceptional, (41 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is SAR 389
SAR 1,158 total
includes taxes & fees
19 Jul - 20 Jul
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
1 bedroom, desk, internet, bed sheets

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (45 reviews)
"Amazing views and beautiful sunsets. "
United States
Erica T.
The price is SAR 631
SAR 1,206 total
includes taxes & fees
16 Aug - 17 Aug
Panoramic Peak: Wintergreen Condo with Views
Outdoor dining

Overlook 180 degree views w/Peloton!

Overlook 180 degree views w/Peloton!
Wintergreen Resort
9.4 out of 10, Exceptional, (3 reviews)
"Excellent stay. Thank you!"
United States
Kimberly B.
Overlook 180 degree views w/Peloton!
Smart TV, fireplace

Bide-a-Wee- Hike the Trails! Close to the slopes!

Bide-a-Wee- Hike the Trails! Close to the slopes!
Wintergreen Resort
9.2 out of 10, Wonderful, (12 reviews)
"Great house close to the village, would stay here again."
United States
David B.
The price is SAR 436
SAR 1,207 total
includes taxes & fees
20 Jul - 21 Jul
Bide-a-Wee- Hike the Trails! Close to the slopes!
Interior

Lofty Pursuits: Spectacular View + EV Charger

Lofty Pursuits: Spectacular View + EV Charger
Treeloft
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay"
United States
David T.
The price is SAR 635
SAR 1,534 total
includes taxes & fees
29 Jul - 30 Jul
Lofty Pursuits: Spectacular View + EV Charger
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wintergreen Hotel Reviews

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

10/10 Excellent
"Beautiful view! The condo was very cleanAnd check in was easy."
Frank S. 2-night trip
Posted 2 days ago
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

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?

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has an outdoor pool, a fireplace, 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. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation. Some other top choices in Wintergreen are 4 BR cabin mins to trails & breweries pets welcome and One of the Best Views in Wintergreen!.

How many vacation rentals are there in Wintergreen?

Choose from 223 Expedia vacation rentals in Wintergreen for a memorable vacation.

What can I see and do in Wintergreen?

While exploring the area, visit family-friendly sights like War Fields, or get outside and enjoy nature at George Washington National Forest. 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.