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Our top choices for Wintergreen holiday homes

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 £244
includes taxes & fees
18 May - 19 May
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

4 BR cabin mins to trails & breweries pets welcome

4 BR cabin mins to trails & breweries pets welcome
Chestnut Springs
9.6 out of 10, Exceptional, (34 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 £429
includes taxes & fees
17 May - 18 May
4 BR cabin mins to trails & breweries pets welcome

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.
The price is £306
includes taxes & fees
19 May - 20 May
Spacious + Serene Mtn Top Escape, 4 En Suites

The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance
Pedlars Edge
9.2 out of 10, Wonderful, (11 reviews)
"This was one of the most well-stocked houses we've ever rented. The owners thought of everything. The house was very comfortable for our group. Access to the Tyro ski slope was 4 houses down, so no need to drive anyone to the slope. The view was beautiful - we would absolutely stay here again!"
United States
Carrie G.
The price is £320
includes taxes & fees
19 May - 20 May
The Distinguished Squirrel Chalet walking distance

Beautiful 4-season Mountain Home- New Listing

Beautiful 4-season Mountain Home- New Listing
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"We had a great time staying here! The place was in great condition and in such a great location! The host was very responsive and helpful with all questions. I would absolutely recommend and will certainly try to book here again in the future!"
United States
Chad H.
The price is £395
includes taxes & fees
18 May - 19 May
Beautiful 4-season Mountain Home- New Listing

"Glass & Pine" Home close to Bold Rock & Vineyards

"Glass & Pine" Home close to Bold Rock & Vineyards
Nellysford
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 £298
includes taxes & fees
7 Jun - 8 Jun
"Glass & Pine" Home close to Bold Rock & Vineyards

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
Chestnut Springs
10.0 out of 10, Exceptional, (17 reviews)
"Perfect spot for a family retreat - highly recommend "
United States
Greg B.
The price is £361
includes taxes & fees
17 May - 18 May
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

Stunning Views, Hot Tub, Impeccable Design

Stunning Views, Hot Tub, Impeccable Design
Wintergreen Resort
10.0 out of 10, Exceptional, (15 reviews)
"Loved the entire home! So cozy and well maintained. The kids loved the downstairs. So easy to the top of the mountain as well. We will be back!!"
United States
Jacquelyn S.
The price is £572
includes taxes & fees
21 May - 22 May
Stunning Views, Hot Tub, Impeccable Design

Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
Nellysford
10.0 out of 10, Exceptional, (5 reviews)
"We really enjoyed our stay! The home was amazing and very well appointed. We enjoyed local breweries and hiking!"
United States
Rachel F.
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

Nowhere Land with Wintergreen Advantage

Nowhere Land with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"The house was fantastic but the hot tub was not working. The control panel was locked and the water temp was 72*. Front desk sent two men out to fix it the next day but they were not able too figure out why it was locked. After googling it we were able to unlock it but the water temp never got above 72. Told the guy at front desk on check out but he didn't do anything to resolve it"
United States
Michael C.
Nowhere Land with Wintergreen Advantage

Mountain Retreat: Year-Round Getaway, Pup Friendly

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
Mountain Retreat: Year-Round Getaway, Pup Friendly

2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds
Laurel Ridge
10.0 out of 10, Exceptional, (4 reviews)
"Fabulous house and we all had a great time! "
United States
Mindy M.
The price is £738
includes taxes & fees
21 May - 22 May
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

Bear Necessities with Wintergreen Advantage

Bear Necessities with Wintergreen Advantage
Pedlars Edge
9.4 out of 10, Exceptional, (3 reviews)
"This is a great cabin at Wintergreen. Ample space for our family of six, great view right off the slope. It’s part of the Wintergreen resort, so staying here gives you access to resort amenities, which is nice. However, because it’s part of the resort and not an independent VRBO, you’re better off booking directly with the resort, you’ll save a bit of money that way and still have all the perks. "
United States
Allen F.
Bear Necessities with Wintergreen Advantage

Whispering Pines with Wintergreen Advantage

Whispering Pines with Wintergreen Advantage
Deer Springs
10.0 out of 10, Exceptional, (1 review)
"We had a great long weekend. Very well- maintained, clean a comfortable home. Nice to have had the golf privileges."
United States
Jennifer B.
The price is £443
includes taxes & fees
22 May - 23 May
Whispering Pines with Wintergreen Advantage

Cabin Blue Ridge with Wintergreen Advantage

Cabin Blue Ridge with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"We were a family group including two elderly folks with some limited mobility. The cabin was easily accessible and easy to navigate for all. The open floor plan was very spacious and comfortable with a great fireplace which came in handy as it was very cold during our stay. I would highly recommend staying here and would not hesitate to book again."
United States
Christian L.
The price is £443
includes taxes & fees
22 May - 23 May
Cabin Blue Ridge with Wintergreen Advantage

Golf Views, Hot Tub & Sleeps 14 - 7th Hole Chalet –

Golf Views, Hot Tub & Sleeps 14 - 7th Hole Chalet –
Wintergreen Resort
8.0 out of 10, Very good, (1 review)
"We enjoyed our stay at the 7th hole chalet and would return. The house is spacious and was clean and included everything we needed. It did seem to have a lot of extra, unnecessary furniture in some of the rooms and pictures weren't exactly like listing. The landscaping was overgrown and messy out front. There are lots of controls for the heating and air throughout the house, but they are very hard to use and no instructions posted. The hot tub was nice and enjoyed by our crew, but the cover lift...
United States
Paula L.
Golf Views, Hot Tub & Sleeps 14 - 7th Hole Chalet –

Chestnut Springs with Wintergreen Advantage

Chestnut Springs with Wintergreen Advantage
Chestnut Springs
8.0 out of 10, Very good, (1 review)
Chestnut Springs with Wintergreen Advantage

Bull City Bungalow with Wintergreen Advantage

Bull City Bungalow with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"Perfect house for a wonderful ski weekend. When we return we will stay here !!!"
United States
David G.
Bull City Bungalow with Wintergreen Advantage

Whispering Elm with Wintergreen Advantage

Whispering Elm with Wintergreen Advantage
Wintergreen
Whispering Elm with Wintergreen Advantage

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Everything was great. "
United States
Nathan T.
The price is £113
includes taxes & fees
17 May - 18 May
Whole House
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

Wintergreen Holiday Homes information

Number of reviews
265
Accommodation
196 Holiday Homes
Lowest Price
£113
Highest Price
£738