Wintergreen Vacation Rentals

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Our top choices for Wintergreen vacation rentals

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (34 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is CA $156
CA $367 total
includes taxes & fees
May 18 - May 19
Wintergreen Condo -Steps to Ski and restaurants

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, (153 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is CA $150
CA $339 total
includes taxes & fees
May 19 - May 20
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

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)
"The place was very clean and spacious. The communication from the hosts was helpful. We had a very pleasant stay."
United States
James S.
Spacious + Serene Mtn Top Escape, 4 En Suites

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, (103 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
Endless Mountain Top Views from All The Way Up!

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (111 reviews)
"Great and comfortable place to stay! Host was very welcoming and responsive. "
United States
Jon L.
The price is CA $228
CA $449 total
includes taxes & fees
May 13 - May 14
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
The price is CA $130
CA $382 total
includes taxes & fees
Jun 4 - Jun 5
Laurelwood Hollow: Walk to Ski & Swim

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.
The price is CA $111
CA $298 total
includes taxes & fees
May 13 - May 14
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.4 out of 10, Exceptional, (14 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is CA $185
CA $449 total
includes taxes & fees
May 18 - May 19
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (49 reviews)
"Great place to stay to hit the ski slopes. Just a short walk to the slopes and right next to the gas station/ small grocery shop to easily pick up some food on the way back from skiing. "
United States
Joyce B.
The price is CA $129
CA $321 total
includes taxes & fees
May 17 - May 18
Where the Trail Ends

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, (127 reviews)
"great stay"
United States
Vickie G.
The price is CA $159
CA $352 total
includes taxes & fees
May 17 - May 18
Escape to the Blue Ridge Mountains at Wine-tergreen!

Mountain Inn Studio 94 with Wintergreen Advantage

Mountain Inn Studio 94 with Wintergreen Advantage
Wintergreen
The price is CA $176
CA $310 total
includes taxes & fees
May 16 - May 17
Mountain Inn Studio 94 with Wintergreen Advantage

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (38 reviews)
"Amazing spot! Ski in - out was so convenient and a quick walk to the village! Phyllis was amazing and the condo was beautiful! Would definitely book this condo again! "
United States
Susan J.
The price is CA $208
CA $559 total
includes taxes & fees
May 17 - May 18
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful stay with great communication with the host "
United States
Annamarie P.
The price is CA $158
CA $523 total
includes taxes & fees
May 13 - May 14
Serenity Cabin-Woodland Retreat

Three Ridges 64 With Wintergreen Advantage

Three Ridges 64 With Wintergreen Advantage
Chestnut Springs
The price is CA $224
CA $414 total
includes taxes & fees
May 13 - May 14
Three Ridges 64 With Wintergreen Advantage

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, (320 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is CA $128
CA $330 total
includes taxes & fees
May 20 - May 21
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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, (30 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
The price is CA $164
CA $341 total
includes taxes & fees
May 17 - May 18
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed it so much! So cozy and close to the resort! "
United States
Katie B.
The price is CA $185
CA $411 total
includes taxes & fees
May 17 - May 18
Cozy Lux Condo at Wintergreen Resort

Mountain Inn Lodge 54 with Wintergreen Advantage

Mountain Inn Lodge 54 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (3 reviews)
"We were in the area looking to possibly relocate and this loft on the mountain was a beautiful stay. Convenient to restaurants within walking distance. We would definitely book again!"
United States
Erin C.
The price is CA $190
CA $347 total
includes taxes & fees
May 14 - May 15
Mountain Inn Lodge 54 with Wintergreen Advantage

Renovated Wintergreen Condo with Pool Access, and more!

Renovated Wintergreen Condo with Pool Access, and more!
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 CA $185
CA $411 total
includes taxes & fees
May 13 - May 14
Renovated Wintergreen Condo with Pool Access, and more!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (32 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
The price is CA $158
CA $465 total
includes taxes & fees
May 18 - May 19
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
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?

Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a patio, a selection of games, and a barbecue grill to put you at ease 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. Some other top choices in Wintergreen are 4 BR cabin mins to trails & breweries pets welcome and Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!.

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.