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Our top choices for Wintergreen holiday homes

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 HK$754
HK$2,941 total
includes taxes & fees
8 May - 9 May
Spacious + Serene Mtn Top Escape, 4 En Suites

Beautiful 4-season Mountain Home- New Listing

Beautiful 4-season Mountain Home- New Listing
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"The house was full of modern appliances, clean and very cozy. Plenty of space and in a great location. "
United States
Scott D.
The price is HK$1,559
HK$4,206 total
includes taxes & fees
11 May - 12 May
Beautiful 4-season Mountain Home- New Listing

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

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 Distinguished Squirrel Chalet walking distance

"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 HK$2,534
HK$4,876 total
includes taxes & fees
16 May - 17 May
"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 HK$1,467
HK$3,839 total
includes taxes & fees
10 May - 11 May
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

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.
4 BR cabin mins to trails & breweries pets welcome

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

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!

Stunning Views, Hot Tub, Impeccable Design

Stunning Views, Hot Tub, Impeccable Design
Wintergreen Resort
10.0 out of 10, Exceptional, (15 reviews)
"This house is beautiful, well kept, and is in a great location near hikes and breweries!"
United States
Lauren M.
The price is HK$2,839
HK$6,409 total
includes taxes & fees
21 May - 22 May
Stunning Views, Hot Tub, Impeccable Design

Red White & WTG: Game Room + Hot Tub

Red White & WTG: Game Room + Hot Tub
Pedlars Edge
10.0 out of 10, Exceptional, (8 reviews)
"House was perfection. Very comfortable beds and every comfort of home is available in this property. Perfect place for two families of four to enjoy a fun weekend on the mountain. "
United States
Kate T.
Red White & WTG: Game Room + Hot Tub

Above The Clouds with Wintergreen Advantage

Above The Clouds with Wintergreen Advantage
Wintergreen
Above The Clouds 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.
Cabin Blue Ridge 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

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (60 reviews)
"The room was very clean and conveniently located for us."
United States
Jeanell S.
The price is HK$649
HK$896 total
includes taxes & fees
10 May - 11 May
The Firefly Springhouse

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Everything was great. "
United States
Nathan T.
The price is HK$705
HK$1,167 total
includes taxes & fees
12 May - 13 May
Whole House

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (16 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is HK$1,007
HK$2,275 total
includes taxes & fees
10 May - 11 May
Historic Bungalow 30 minutes from Wintergreen

NEW! Cheerful 2 bd bungalow with hot tub. Must see!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.8 out of 10, Exceptional, (55 reviews)
"Our host did a great job!! She thought of everything to make your stay enjoyable. We will definitely be returning."
United States
Cora S.
The price is HK$1,019
HK$1,744 total
includes taxes & fees
21 May - 22 May
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
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 Vacation Homes information

Number of reviews
397
Accommodation
187 Vacation Homes
Lowest Price
HK$896
Highest Price
HK$7,846

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