Wintergreen Vacation Rentals

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Our top choices for Wintergreen vacation rentals

9.6 out of 10, Exceptional, (149 reviews)
"Very clean and pet-friendly "
United States
Heston
$215 nightly
The price is $241
Mar 19 - Mar 20
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
10.0 out of 10, Exceptional, (98 reviews)
"Highly recommend staying at this beautiful condo! The kitchen has everything you need, the views are breath-taking, the condo is very clean, and the hosts are very communicative and helpful. Will definitely stay here again the next time we travel to the area!"
United States
Allison N.
$230 nightly
The price is $259
Mar 19 - Mar 20
Total with taxes and fees
Endless Mountain Top Views from All The Way Up!

Apartment in Wintergreen Resort

Laurelwood Hollow: Walk to Ski & Swim
10.0 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
$265 nightly
The price is $279
Mar 19 - Mar 20
Total with taxes and fees
Laurelwood Hollow: Walk to Ski & Swim
9.8 out of 10, Exceptional, (32 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
$236 nightly
The price is $265
Mar 19 - Mar 20
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
9.0 out of 10, Wonderful, (316 reviews)
"Gorgeous view. Our fourth time here, and still a lovely place. "
United States
Elaine B.
$220 nightly
The price is $247
Mar 19 - Mar 20
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
10.0 out of 10, Exceptional, (28 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
$279 nightly
The price is $313
Apr 16 - Apr 17
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
9.6 out of 10, Exceptional, (40 reviews)
"Very clean, well organized, excellent views"
United States
Guy M.
$259 nightly
The price is $291
Mar 19 - Mar 20
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
9.8 out of 10, Exceptional, (30 reviews)
"Great communication from the startReturn texts the same day on any questionsGreat location for our tripVery cleanViews around property are greatNice restaurant A plus for what we neededDog friendly Thanks againHope to be back"
United States
Phil P.
$216 nightly
The price is $243
Mar 19 - Mar 20
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Condo in Wintergreen Resort

The Modern Mountain Condo
10.0 out of 10, Exceptional, (46 reviews)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
$204 nightly
The price is $229
Mar 19 - Mar 20
Total with taxes and fees
The Modern Mountain Condo

Vacation Home in Wintergreen Resort

Spacious + Serene Mtn Top Escape, 4 En Suites
10.0 out of 10, Exceptional, (51 reviews)
"Fabulous getaway at this beautiful property--clean, well maintained and easy communication with host. Stocked kitchen, comfortable beds, views, and great location. Book here-you will not be disappointed. Thank you Mary and Tyler...we are sure to return!"
United States
Jackie S.
$331 nightly
The price is $372
Mar 19 - Mar 20
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
9.4 out of 10, Exceptional, (11 reviews)
"Beautiful view!"
United States
Serge L.
$259 nightly
The price is $291
Mar 19 - Mar 20
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views
9.4 out of 10, Exceptional, (13 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
$288 nightly
The price is $323
Mar 19 - Mar 20
Total with taxes and fees
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
10.0 out of 10, Exceptional, (104 reviews)
"We had a great time! The host was very responsive and great location! "
United States
Tess B.
$218 nightly
The price is $245
Mar 19 - Mar 20
Total with taxes and fees
Wintergreen. Sunset Vista Villa - Close to the ski slopes

Apartment in Wintergreen Resort

Wintergreen Resort Condo Available Now!!
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.
$316 nightly
The price is $320
Mar 19 - Mar 20
Total with taxes and fees
Wintergreen Resort Condo Available Now!!
10.0 out of 10, Exceptional, (13 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
$191 nightly
The price is $214
Mar 19 - Mar 20
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Cabin in Nellysford

Blackwood Chalet
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
$345 nightly
The price is $363
Mar 19 - Mar 20
Total with taxes and fees
Blackwood Chalet
10.0 out of 10, Exceptional, (34 reviews)
"The home was clean and in a great location to explore the Wintergreen area. Host was welcoming and responsive."
United States
Rob M.
$290 nightly
The price is $326
Mar 19 - Mar 20
Total with taxes and fees
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
9.8 out of 10, Exceptional, (126 reviews)
"Everything was as is listed, we were off season so hiking and scenic views is what there was to do, relaxing. Host was accessible on phone, place was clean. "
United States
David L.
$229 nightly
The price is $257
Mar 23 - Mar 24
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
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
$198 nightly
The price is $222
Mar 19 - Mar 20
Total with taxes and fees
Mountain Inn Studio 96 with Wintergreen Advantage
10.0 out of 10, Exceptional, (9 reviews)
"Great little ski and ski out Property"
United States
Richard
$173 nightly
The price is $194
Mar 19 - Mar 20
Total with taxes and fees
Little Mountain Haven. True ski-in, ski-out. First floor!
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

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 $229 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?

4 BR cabin mins to trails & breweries pets welcome: Visitors give good reviews to this Wintergreen vacation home rental, which offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Some other top choices in Wintergreen are Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope and Insane Mountain Views - New Listing.

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 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.