Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Wintergreen vacation rentals

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, (101 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
The price is ￥13,609
￥38,510 total
includes taxes & fees
Apr 12 - Apr 13
Endless Mountain Top Views from All The Way Up!
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, (149 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is ￥17,500
￥38,412 total
includes taxes & fees
Apr 12 - Apr 13
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Exterior

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

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (106 reviews)
"Great stay with a fabulous view! Very cozy and comfortable! We had a wonderful little getaway!"
United States
Vicki E.
The price is ￥21,477
￥45,022 total
includes taxes & fees
Apr 13 - Apr 14
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (33 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is ￥18,136
￥42,163 total
includes taxes & fees
Apr 12 - Apr 13
Wintergreen Condo -Steps to Ski and restaurants

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, (317 reviews)
"I love this place!!! Will book again everytime we are there!"
United States
Thavikiet T.
The price is ￥16,466
￥39,575 total
includes taxes & fees
Apr 12 - Apr 13
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
1 bedroom, desk, internet, bed sheets

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.8 out of 10, Exceptional, (41 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
The price is ￥22,114
￥46,273 total
includes taxes & fees
Apr 12 - Apr 13
Panoramic Peak: Wintergreen Condo with Views
Property grounds

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, (13 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is ￥12,886
￥34,123 total
includes taxes & fees
Apr 12 - Apr 13
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Fireplace

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (47 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 ￥14,999
￥36,495 total
includes taxes & fees
Apr 19 - Apr 20
The Modern Mountain Condo
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, (30 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
The price is ￥19,091
￥38,591 total
includes taxes & fees
Apr 13 - Apr 14
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
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, (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.
The price is ￥18,470
￥41,110 total
includes taxes & fees
Apr 12 - Apr 13
Escape to the Blue Ridge Mountains at Wine-tergreen!
Fridge, microwave, oven, stovetop

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (34 reviews)
"Cozy, clean very attentive host Paul was amazingThis cozy kid friendly family home was very accommodating. Def will be back again!!"
United States
Pamela P.
The price is ￥16,466
￥48,686 total
includes taxes & fees
Apr 13 - Apr 14
Retreat @ 3 Ridges / 3 min walk -> Slopes & 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, (54 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.
The price is ￥12,679
￥56,403 total
includes taxes & fees
Apr 12 - Apr 13
Spacious + Serene Mtn Top Escape, 4 En Suites
Smart TV

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (11 reviews)
"Great house and great host!"
United States
Joe B.
The price is ￥18,396
￥59,965 total
includes taxes & fees
Apr 13 - Apr 14
Serenity Cabin-Woodland Retreat
TV, fireplace

Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful condo"
United States
Mary C.
The price is ￥22,114
￥46,273 total
includes taxes & fees
Apr 12 - Apr 13
Mountain View Vista: Resort Condo w/ Views
Exterior

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, (31 reviews)
"Well stocked house with great layout for families or two couples. Great kitchen setup with everything you’ll need. Close to the resort and skiing. Close to hiking trails. "
United States
Jeremiah H.
The price is ￥17,201
￥50,974 total
includes taxes & fees
Apr 29 - Apr 30
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
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.
The price is ￥15,131
￥44,461 total
includes taxes & fees
May 11 - May 12
Laurelwood Hollow: Walk to Ski & Swim
Fridge, microwave, oven, stovetop

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 ￥21,477
￥51,454 total
includes taxes & fees
Apr 12 - Apr 13
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Cabin, Private Bathroom (Blackwood Chalet) | Lounge

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is ￥25,642
￥60,650 total
includes taxes & fees
Apr 13 - Apr 14
Blackwood Chalet
TV, fireplace

Wintergreen Resort Condo Available Now!!

Wintergreen Resort Condo Available Now!!
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 ￥24,659
￥50,977 total
includes taxes & fees
Apr 12 - Apr 13
Wintergreen Resort Condo Available Now!!
Smart TV, fireplace, table tennis, books

4 BR cabin mins to trails & breweries pets welcome

4 BR cabin mins to trails & breweries pets welcome
Chestnut Springs
9.4 out of 10, Exceptional, (33 reviews)
"Beautiful place. Exactly as depicted in the listing. Very responsive host with questions prior to my stay."
United States
Philip S.
The price is ￥30,784
￥93,173 total
includes taxes & fees
Apr 12 - Apr 13
4 BR cabin mins to trails & breweries pets welcome
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

Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope

Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope

10/10 Excellent
"Beautiful view, thank you for the memories"
Will C. 2-night trip
Posted 5 hours ago
Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope

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?

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 Upscale and Family-Friendly in Wintergreen and Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14.

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.