Wintergreen Vacation Rentals

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Our top choices for Wintergreen vacation rentals

Apartment in Wintergreen Resort

Laurelwood Hollow: Walk to Ski & Swim
10.0 out of 10, Exceptional, (7 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.
The price is ¥13,144
¥41,431 total
includes taxes & fees
Feb 25 - Feb 26
Laurelwood Hollow: Walk to Ski & Swim
10.0 out of 10, Exceptional, (24 reviews)
"The house was so nice and clean and the host was great also and we had a great stay and would highly recommend it. "
United States
Jody W.
The price is ¥29,227
¥71,376 total
includes taxes & fees
Feb 25 - Feb 26
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
9.0 out of 10, Wonderful, (312 reviews)
"The house qas very clean, furniture comfortable, and the atea beautiful "
United States
Natalie R.
The price is ¥16,005
¥39,162 total
includes taxes & fees
Feb 25 - Feb 26
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
10.0 out of 10, Exceptional, (97 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.
The price is ¥18,489
¥45,076 total
includes taxes & fees
Feb 25 - Feb 26
Endless Mountain Top Views from All The Way Up!

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.
The price is ¥23,969
¥49,551 total
includes taxes & fees
Feb 25 - Feb 26
Wintergreen Resort Condo Available Now!!
10.0 out of 10, Exceptional, (102 reviews)
"We had a great time! The host was very responsive and great location! "
United States
Tess B.
The price is ¥22,268
¥45,846 total
includes taxes & fees
Feb 25 - Feb 26
Wintergreen. Sunset Vista Villa - Close to the ski slopes
9.8 out of 10, Exceptional, (29 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.
The price is ¥18,557
¥37,511 total
includes taxes & fees
Mar 1 - Mar 2
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
9.8 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is ¥18,557
¥47,062 total
includes taxes & fees
Feb 25 - Feb 26
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
9.6 out of 10, Exceptional, (147 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is ¥17,010
¥37,337 total
includes taxes & fees
Mar 16 - Mar 17
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Condo in Wintergreen Resort

The Modern Mountain Condo
10.0 out of 10, Exceptional, (44 reviews)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
The price is ¥14,579
¥35,474 total
includes taxes & fees
Mar 5 - Mar 6
The Modern Mountain Condo
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed it so much! So cozy and close to the resort! "
United States
Katie B.
The price is ¥24,433
¥50,015 total
includes taxes & fees
Feb 25 - Feb 26
Cozy Cute Condo in Wintergreen Resort
9.8 out of 10, Exceptional, (30 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is ¥18,557
¥41,332 total
includes taxes & fees
Mar 9 - Mar 10
Wintergreen Condo -Steps to Ski and restaurants
10.0 out of 10, Exceptional, (44 reviews)
"Cute little place. Well stocked, easy access, and very convenient to wintergreen facilities. "
United States
david
The price is ¥20,876
¥45,151 total
includes taxes & fees
Feb 25 - Feb 26
Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking

Vacation Home in Wintergreen Resort

Beautiful 4-season Mountain Home- New Listing
10.0 out of 10, Exceptional, (43 reviews)
"The property is clean, bed rooms are spacious. 3.5 bath, kitchen has latest appliances, bedding & accessories are star hotel standard. We loved our stay. "
United States
Mridul G.
The price is ¥30,773
¥83,010 total
includes taxes & fees
Mar 2 - Mar 3
Beautiful 4-season Mountain Home- New Listing
9.8 out of 10, Exceptional, (124 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.
The price is ¥17,954
¥39,961 total
includes taxes & fees
Mar 1 - Mar 2
Escape to the Blue Ridge Mountains at Wine-tergreen!
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wished we could have stayed longer! The place was super clean and the views were beautiful once the rain finally stopped! Close to our favorite brewery and cidery. There were issues with TV reception (buffering) which may just be the area. Not much time for TV watching anyway with all the beautiful things to explore. We enjoyed our stay. "
United States
Robert H.
The price is ¥26,791
¥63,493 total
includes taxes & fees
Mar 2 - Mar 3
"Glass & Pine" Home close to Bold Rock & Vineyards
9.2 out of 10, Wonderful, (10 reviews)
"It was so clean and comfortable. Waking up early in the working to watch the sunrise over the mountains was majestic. Highly recommend this get away!"
United States
Cindy
The price is ¥21,495
¥44,979 total
includes taxes & fees
Feb 25 - Feb 26
Mountain View Vista: Resort Condo w/ Views

Cabin in Nellysford

Blackwood Chalet
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is ¥23,969
¥57,846 total
includes taxes & fees
Feb 25 - Feb 26
Blackwood Chalet
10.0 out of 10, Exceptional, (34 reviews)
"Great"
United States
Daniel W.
The price is ¥22,299
¥61,223 total
includes taxes & fees
Mar 8 - Mar 9
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Vacation Home in Wintergreen Resort

Spacious + Serene Mtn Top Escape, 4 En Suites
10.0 out of 10, Exceptional, (50 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.
The price is ¥11,423
¥53,640 total
includes taxes & fees
Feb 25 - Feb 26
Spacious + Serene Mtn Top Escape, 4 En Suites
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

Search for holiday rentals in Wintergreen on Expedia! You can easily find your home rentals, villas, holiday apartments in Wintergreen using one of the methods below:

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Look no further and take a look at our great range of rental properties in Wintergreen!

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 The newest and largest edition to the Wintergreen Retreat portfolio! and One of the Best Views in Wintergreen!.

How many vacation rentals are there in Wintergreen?

Choose from 227 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.