Beautiful small lake surrounded with wintergreen forest. Dajicko lake on Golija Mountain in Serbia

Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Wintergreen vacation rentals

Fireplace

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (54 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.
$185 nightly
The price is $208
Jun 24 - Jun 25
Total with taxes and fees
Where the Trail Ends
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)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
$259 nightly
The price is $291
Jun 23 - Jun 24
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
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, (116 reviews)
"Great location"
United States
Chrissy R.
$270 nightly
The price is $303
Jun 23 - Jun 24
Total with taxes and fees
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, (155 reviews)
"Lisa we are happy for staying at your places it awesome and we had great time, thank you let us use your home"
United States
Issac S.
$221 nightly
The price is $248
Jun 23 - Jun 24
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
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, (108 reviews)
"Nice place!"
United States
Gregory G.
$223 nightly
The price is $250
Jun 25 - Jun 26
Total with taxes and fees
Endless Mountain Top Views from All The Way Up!
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.
$230 nightly
The price is $258
Jun 23 - Jun 24
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
1 bedroom, iron/ironing board, free WiFi, bed sheets

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, (14 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
$199 nightly
The price is $223
Jun 23 - Jun 24
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

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, (324 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
$216 nightly
The price is $242
Jun 25 - Jun 26
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
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.
$199 nightly
The price is $223
Jul 1 - Jul 2
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
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.
$239 nightly
The price is $268
Jun 23 - Jun 24
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (9 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
$275 nightly
The price is $290
Jul 19 - Jul 20
Total with taxes and fees
Laurelwood Hollow: Walk to Ski & Swim
Fridge, microwave, oven, stovetop

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, (39 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
$275 nightly
The price is $308
Jun 23 - Jun 24
Total with taxes and fees
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
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.
$334 nightly
The price is $375
Jun 23 - Jun 24
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
Fridge, microwave, oven, stovetop

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.
$266 nightly
The price is $299
Jun 25 - Jun 26
Total with taxes and fees
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
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.
$264 nightly
The price is $303
Jun 23 - Jun 24
Total with taxes and fees
Bide-a-Wee- Hike the Trails! Close to the slopes!
Smart TV, fireplace, books

Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo

Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"A great place to stay for a couple days. Small kitchen but equipped. Very clean place. Attentive service from the host."
United States
Jean H.
$218 nightly
The price is $245
Jun 30 - Jul 1
Total with taxes and fees
Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo
Outdoor spa tub

Bear Tracks Cottage: New Hot Tub + Fire Pit

Bear Tracks Cottage: New Hot Tub + Fire Pit
Nellysford
10.0 out of 10, Exceptional, (33 reviews)
"We loved the location! This cabin has everything you need for the perfect mountain getaway."
United States
Amanda
$404 nightly
The price is $454
Jun 23 - Jun 24
Total with taxes and fees
Bear Tracks Cottage: New Hot Tub + Fire Pit
Property grounds

Luxury Condo in the Sky! Finest in Wintergreen!

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (34 reviews)
"Amazing place with even more amazing views. Very comfortable and beautiful place. We had high expectations based on the pictures in the listing, and the place exceeded these high expectations. Fantastic place."
United States
missy s.
$278 nightly
The price is $312
Jul 2 - Jul 3
Total with taxes and fees
Luxury Condo in the Sky! Finest in Wintergreen!
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.
$244 nightly
The price is $280
Jun 23 - Jun 24
Total with taxes and fees
Overlook 180 degree views w/Peloton!
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.
$259 nightly
The price is $291
Jun 23 - Jun 24
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views
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

Where the Trail Ends

Where the Trail Ends

10/10 Excellent
"Great location, nice condo, clean, comfortable and easy communication w owner."
Todd H. 1-night trip
Posted 8 hours ago
Where the Trail Ends

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 $208 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?

One of the Best Views in Wintergreen!: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has an indoor pool, a fireplace, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a patio and an outdoor tennis court. Some other top choices in Wintergreen are Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort! and Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill.

How many vacation rentals are there in Wintergreen?

Choose from 224 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 Stoney Creek Golf Course 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.