Search Vacation Homes in Wintergreen

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Wintergreen vacation 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 ¥15,109
¥58,932 total
includes taxes & fees
May 6 - May 7
Spacious + Serene Mtn Top Escape, 4 En Suites

"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 ¥27,202
¥64,467 total
includes taxes & fees
May 6 - May 7
"Glass & Pine" Home close to Bold Rock & Vineyards

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 ¥17,127
¥52,206 total
includes taxes & fees
May 25 - May 26
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

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 ¥31,245
¥84,283 total
includes taxes & fees
May 11 - May 12
Beautiful 4-season Mountain Home- New Listing

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, (17 reviews)
"Perfect spot for a family retreat - highly recommend "
United States
Greg B.
The price is ¥29,400
¥77,096 total
includes taxes & fees
May 6 - May 7
Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin

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 ¥28,092
¥67,707 total
includes taxes & fees
May 11 - May 12
The Distinguished Squirrel Chalet walking distance

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 ¥33,757
¥96,801 total
includes taxes & fees
May 19 - May 20
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
The price is ¥39,253
¥88,515 total
includes taxes & fees
May 6 - May 7
Mountain Retreat: Year-Round Getaway, Pup Friendly

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 ¥35,327
¥109,849 total
includes taxes & fees
Jun 2 - Jun 3
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 ¥58,361
¥157,227 total
includes taxes & fees
May 6 - May 7
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)
"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.
The price is ¥70,592
¥154,313 total
includes taxes & fees
May 6 - May 7
Red White & WTG: Game Room + Hot Tub

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 ¥45,376
¥94,561 total
includes taxes & fees
May 22 - May 23
Cabin Blue Ridge 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 ¥14,131
¥23,380 total
includes taxes & fees
May 6 - May 7
Whole House

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (59 reviews)
"The room was very clean and conveniently located for us."
United States
Jeanell S.
The price is ¥13,000
¥17,965 total
includes taxes & fees
May 6 - May 7
The Firefly Springhouse

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 ¥17,664
¥29,272 total
includes taxes & fees
May 11 - May 12
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

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 ¥18,395
¥32,373 total
includes taxes & fees
May 10 - May 11
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

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 ¥19,840
¥45,378 total
includes taxes & fees
May 6 - May 7
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)
"Lovely cozy place in the mountains, we had a total blast!"
United States
Prabir
The price is ¥21,196
¥38,439 total
includes taxes & fees
May 7 - May 8
Cozy Country small two bedroom home.

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

Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
Nellysford
9.8 out of 10, Exceptional, (8 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 ¥16,486
¥46,726 total
includes taxes & fees
May 6 - May 7
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 ¥10,224
¥52,741 total
includes taxes & fees
May 6 - May 7
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Wintergreen Hotel Reviews

Find out more about Wintergreen

Wintergreen Vacation Homes information

Number of reviews
440
Accommodation
196 Vacation Homes
Lowest Price
¥17,965
Highest Price
¥157,227

Explore a world of travel with Expedia