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Our top choices for Wintergreen vacation 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, (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 ¥17,133
¥51,485 total
includes taxes & fees
Apr 20 - Apr 21
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-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, (55 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 ¥20,046
¥65,980 total
includes taxes & fees
May 19 - May 20
Spacious + Serene Mtn Top Escape, 4 En Suites

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 ¥30,697
¥93,622 total
includes taxes & fees
Apr 19 - Apr 20
4 BR cabin mins to trails & breweries pets welcome

"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 ¥27,484
¥65,136 total
includes taxes & fees
Apr 27 - Apr 28
"Glass & Pine" Home close to Bold Rock & Vineyards

Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin

Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin
Chestnut Springs
10.0 out of 10, Exceptional, (16 reviews)
"Perfect spot for a family retreat - highly recommend "
United States
Greg B.
The price is ¥25,462
¥72,956 total
includes taxes & fees
Apr 19 - Apr 20
Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin

Beautiful 4-season Mountain Home- New Listing

Beautiful 4-season Mountain Home- New Listing
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place to say, luxurious and family friendly. Second time our family has stayed at the unit and look forward to hopefully doing so again. "
United States
Timothy G.
The price is ¥31,569
¥85,337 total
includes taxes & fees
Apr 20 - Apr 21
Beautiful 4-season Mountain Home- New Listing

The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance
Pedlars Edge
9.2 out of 10, Wonderful, (11 reviews)
"we appreciated that it was stocked with basic spices, coffee, necessary cookware, etc. Nice location "
United States
Ryan R.
The price is ¥33,981
¥76,354 total
includes taxes & fees
Apr 20 - Apr 21
The Distinguished Squirrel Chalet walking distance

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.
The price is ¥47,592
¥126,311 total
includes taxes & fees
Apr 20 - Apr 21
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

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 ¥61,587
¥162,336 total
includes taxes & fees
Apr 19 - Apr 20
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

Red White & WTG: Game Room + Hot Tub

Red White & WTG: Game Room + Hot Tub
Pedlars Edge
10.0 out of 10, Exceptional, (8 reviews)
"I liked the following: -spacious house -supplies on hand -cleanliness of the house -location -quietness -# of bathrooms and bedrooms -no pets rule -no smoking rule -house decor"
United States
Deran
The price is ¥71,229
¥162,653 total
includes taxes & fees
Apr 19 - Apr 20
Red White & WTG: Game Room + Hot Tub

Mountain Retreat: Year-Round Getaway, Pup Friendly

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is ¥39,977
¥89,790 total
includes taxes & fees
Apr 20 - Apr 21
Mountain Retreat: Year-Round Getaway, Pup Friendly

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Everything was great. "
United States
Nathan T.
The price is ¥14,278
¥23,623 total
includes taxes & fees
Apr 22 - Apr 23
Whole House

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (33 reviews)
"This was a wonderful, private, modern place to stay! We were here for a visit to Pippin Hill and this was the perfect place!"
United States
Shiloh F.
The price is ¥28,397
¥66,096 total
includes taxes & fees
Apr 20 - Apr 21
Hillside Haven: Modern Retreat, Mountain Views

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Waynesboro
10.0 out of 10, Exceptional, (20 reviews)
"The perfect stay for a wedding weekend in Waynesboro. It was very warm and accommodating and I can’t say enough good things about it. Thank you for a great weekend"
United States
Michael W.
The price is ¥17,847
¥29,575 total
includes taxes & fees
Apr 22 - Apr 23
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (57 reviews)
"The room was very clean and conveniently located for us."
United States
Jeanell S.
The price is ¥13,135
¥18,151 total
includes taxes & fees
Apr 20 - Apr 21
The Firefly Springhouse

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (15 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is ¥20,388
¥45,880 total
includes taxes & fees
Apr 19 - Apr 20
Historic Bungalow 30 minutes from Wintergreen

Cozy Country small two bedroom home.

Cozy Country small two bedroom home.
Roseland
9.8 out of 10, Exceptional, (19 reviews)
"Wonderful property within a short drive to the resort for snowboarding. Had everything you would need f9"
United States
Melissa R.
The price is ¥21,416
¥38,303 total
includes taxes & fees
Apr 20 - Apr 21
Cozy Country small two bedroom home.

Fox Hill: Hot Tub, Views, Pet Friendly!

Fox Hill: Hot Tub, Views, Pet Friendly!
Afton
10.0 out of 10, Exceptional, (15 reviews)
"Everything was perfect. We needed a night away and this was the perfect place to end up."
United States
Dave D.
The price is ¥36,329
¥81,775 total
includes taxes & fees
Apr 20 - Apr 21
Fox Hill: Hot Tub, Views, Pet Friendly!

Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
Nellysford
10.0 out of 10, Exceptional, (7 reviews)
"Adorable, clean and quiet stay! The place was nicer than expected. It's obvious the hosts are thoughtful of their guests - we found everything we needed and more. A short drive into Nellysford and tucked away in the trees. "
United States
Katie K.
The price is ¥16,657
¥47,211 total
includes taxes & fees
Apr 19 - Apr 20
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Secluded 20+ Acre Retreat Near Brew & Wine Trails

Secluded 20+ Acre Retreat Near Brew & Wine Trails
Afton
10.0 out of 10, Exceptional, (13 reviews)
"Everything was exactly as stated. We loved the house and the close proximity to the 151. We will definitely come back! "
United States
Harold R.
The price is ¥11,411
¥54,682 total
includes taxes & fees
Apr 19 - Apr 20
Secluded 20+ Acre Retreat Near Brew & Wine Trails
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
375
Accommodation
197 Vacation Homes
Lowest Price
¥18,151
Highest Price
¥162,653

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