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Our top choices for Wintergreen vacation homes

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

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (28 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
The price is ¥17,049
¥51,587 total
includes taxes & fees
Mar 17 - Mar 18
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

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, (31 reviews)
"Nice place and very clean "
United States
Melad K.
The price is ¥30,546
¥92,452 total
includes taxes & fees
Mar 12 - Mar 13
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 ¥27,401
¥64,939 total
includes taxes & fees
Mar 24 - Mar 25
"Glass & Pine" Home close to Bold Rock & Vineyards

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (50 reviews)
"Fabulous getaway at this beautiful property--clean, well maintained and easy communication with host. Stocked kitchen, comfortable beds, views, and great location. Book here-you will not be disappointed. Thank you Mary and Tyler...we are sure to return!"
United States
Jackie S.
The price is ¥18,601
¥63,694 total
includes taxes & fees
Mar 15 - Mar 16
Spacious + Serene Mtn Top Escape, 4 En Suites

The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance
Pedlars Edge
9.0 out of 10, Wonderful, (10 reviews)
"we appreciated that it was stocked with basic spices, coffee, necessary cookware, etc. Nice location "
United States
Ryan R.
The price is ¥32,985
¥74,756 total
includes taxes & fees
Mar 18 - Mar 19
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, (43 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 ¥31,414
¥83,854 total
includes taxes & fees
Apr 7 - Apr 8
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, (16 reviews)
"Perfect spot for a family retreat - highly recommend "
United States
Greg B.
The price is ¥41,800
¥92,943 total
includes taxes & fees
Mar 15 - Mar 16
Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin

Whiskey Ridge - Luxury Mountaintop Family Retreat * Dog Friendly * Hot Tub

Whiskey Ridge - Luxury Mountaintop Family Retreat * Dog Friendly * Hot Tub
Wintergreen Resort
10.0 out of 10, Exceptional, (11 reviews)
"House had everything we could possibly want. The layout was perfect for teens to have their own space."
United States
Jessica S.
The price is ¥37,294
¥98,831 total
includes taxes & fees
Mar 12 - Mar 13
Whiskey Ridge - Luxury Mountaintop Family Retreat * Dog Friendly * Hot Tub

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 ¥47,448
¥123,086 total
includes taxes & fees
Mar 12 - Mar 13
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
Wintergreen Resort
10.0 out of 10, Exceptional, (59 reviews)
"Great stay, lot of fun"
United States
Cooper B.
The price is ¥83,034
¥165,004 total
includes taxes & fees
Mar 29 - Mar 30
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

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 ¥43,858
¥138,058 total
includes taxes & fees
Mar 17 - Mar 18
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

Serene Wintergreen Retreat, Nestled in the Trees

Serene Wintergreen Retreat, Nestled in the Trees
Wintergreen Resort
9.6 out of 10, Exceptional, (19 reviews)
"A great weekend stay with our guests and family as well as the dogs! The only thing I could find to complain about was that the balcony area was piled with leaves when we arrived but other than that it wasn't much of a bother. The kids had fun throwing the leaves back into the woods. It was spacious and our host was very communicative. Would come to stay again!"
United States
Samantha Mae S.
The price is ¥97,150
¥177,835 total
includes taxes & fees
Mar 14 - Mar 15
Serene Wintergreen Retreat, Nestled in the Trees

Family-Friendly Meets Luxury

Family-Friendly Meets Luxury
Pedlars Edge
9.8 out of 10, Exceptional, (7 reviews)
"Great Spot for Family gathering"
United States
Ary S.
The price is ¥83,034
¥185,074 total
includes taxes & fees
Apr 1 - Apr 2
Family-Friendly Meets Luxury

Designer Home w/ Incredible Views, Sleeps 16

Designer Home w/ Incredible Views, Sleeps 16
Wintergreen Resort
9.2 out of 10, Wonderful, (17 reviews)
"Beautiful mountain getaway in the heart of Wintergreen with amazing views!"
United States
Alex d.
The price is ¥82,877
¥179,760 total
includes taxes & fees
Mar 29 - Mar 30
Designer Home w/ Incredible Views, Sleeps 16

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Beautiful and cozy place. We booked this place to visit with our grand-daughters. Host was delightful and very sweet. The keypad to get in was a little wonky but the host has a back up plan that works every time. "
United States
Chris W.
The price is ¥14,207
¥23,507 total
includes taxes & fees
Mar 15 - Mar 16
Whole House

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (49 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is ¥13,071
¥18,063 total
includes taxes & fees
Mar 12 - Mar 13
The Firefly Springhouse

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, (48 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
The price is ¥18,470
¥31,978 total
includes taxes & fees
Mar 15 - Mar 16
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (33 reviews)
"Fantastic property with all the amenities near UVA, and lots of wineries."
United States
roberto c.
The price is ¥28,257
¥65,771 total
includes taxes & fees
Mar 12 - Mar 13
Hillside Haven: Modern Retreat, Mountain Views

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 ¥19,594
¥44,874 total
includes taxes & fees
Mar 12 - Mar 13
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, (18 reviews)
"Lovely cozy place in the mountains, we had a total blast!"
United States
Prabir
The price is ¥21,311
¥38,115 total
includes taxes & fees
Mar 12 - Mar 13
Cozy Country small two bedroom home.
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
367
Accommodation
197 Vacation Homes
Lowest Price
¥23,507
Highest Price
¥185,074

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