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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, (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 ¥11,312
¥54,209 total
includes taxes & fees
Mar 4 - Mar 5
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 ¥27,247
¥64,573 total
includes taxes & fees
Mar 4 - Mar 5
"Glass & Pine" Home close to Bold Rock & Vineyards

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, (27 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
The price is ¥18,514
¥52,406 total
includes taxes & fees
Mar 17 - Mar 18
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

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 ¥31,054
¥83,768 total
includes taxes & fees
Mar 4 - Mar 5
Beautiful 4-season Mountain Home- New Listing

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 ¥42,109
¥87,543 total
includes taxes & fees
Mar 17 - Mar 18
The Distinguished Squirrel Chalet walking distance

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
Wintergreen Resort
10.0 out of 10, Exceptional, (58 reviews)
"Great stay, lot of fun"
United States
Cooper B.
The price is ¥33,588
¥101,831 total
includes taxes & fees
Mar 8 - Mar 9
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

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 ¥30,196
¥91,393 total
includes taxes & fees
Mar 15 - Mar 16
4 BR cabin mins to trails & breweries pets welcome

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 ¥36,867
¥97,698 total
includes taxes & fees
Mar 15 - Mar 16
Whiskey Ridge - Luxury Mountaintop Family Retreat * Dog Friendly * Hot Tub

Ridge Retreat @ Wintergreen!

Ridge Retreat @ Wintergreen!
Wintergreen Resort
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful home and it has everything you need for a get-a-way. Five couples and plenty of room to have your own space. Close to lots of recreation and entertainment. "
United States
Robert J.
The price is ¥39,003
¥118,803 total
includes taxes & fees
Mar 9 - Mar 10
Ridge Retreat @ Wintergreen!

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 ¥46,815
¥119,867 total
includes taxes & fees
Mar 4 - Mar 5
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 ¥43,611
¥137,281 total
includes taxes & fees
Mar 10 - Mar 11
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)
"Very clean, check in was so easy and so was checkout! Very close to the slopes. Will stay here again."
United States
Taylor
The price is ¥70,614
¥159,836 total
includes taxes & fees
Mar 4 - Mar 5
Red White & WTG: Game Room + Hot Tub

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 ¥82,567
¥184,033 total
includes taxes & fees
Apr 1 - Apr 2
Family-Friendly Meets Luxury

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 ¥96,603
¥176,834 total
includes taxes & fees
Mar 14 - Mar 15
Serene Wintergreen Retreat, Nestled in the Trees

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 ¥82,567
¥179,088 total
includes taxes & fees
Mar 29 - Mar 30
Designer Home w/ Incredible Views, Sleeps 16

Wintergreen Luxury, Breathtaking Views

Wintergreen Luxury, Breathtaking Views
Wintergreen Resort
10.0 out of 10, Exceptional, (6 reviews)
"We rented this home for 3 nights for a 45th birthday party with some friends. The views are outstanding. The back deck has a giant jacuzzi and a sauna plus lots of room to relax. There are 6 comfortable bedrooms plus living room. The house had everything we need and I would highly recommend! "
United States
Daniil K.
The price is ¥115,593
¥226,420 total
includes taxes & fees
Apr 1 - Apr 2
Wintergreen Luxury, Breathtaking Views

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Angela was very responsive to any questions that I had.The house was well stocked and cozy. Very convenient location as well. "
United States
Sheri C.
The price is ¥14,045
¥23,238 total
includes taxes & fees
Mar 4 - Mar 5
Whole House

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 ¥18,258
¥31,611 total
includes taxes & fees
Mar 5 - Mar 6
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

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, (19 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 ¥25,478
¥37,984 total
includes taxes & fees
Apr 3 - Apr 4
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, (49 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is ¥12,921
¥17,855 total
includes taxes & fees
Mar 8 - Mar 9
The Firefly Springhouse
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
418
Accommodation
197 Vacation Homes
Lowest Price
¥17,855
Highest Price
¥226,420

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