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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, (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 HK$533
HK$2,655 total
includes taxes & fees
15 Mar - 16 Mar
Spacious + Serene Mtn Top Escape, 4 En Suites

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 HK$845
HK$2,558 total
includes taxes & fees
18 Mar - 19 Mar
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 HK$1,558
HK$4,202 total
includes taxes & fees
16 Mar - 17 Mar
Beautiful 4-season Mountain Home- New Listing

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 HK$1,515
HK$4,585 total
includes taxes & fees
15 Mar - 16 Mar
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 HK$1,356
HK$3,214 total
includes taxes & fees
24 Mar - 25 Mar
"Glass & Pine" Home close to Bold Rock & Vineyards

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 HK$1,628
HK$3,697 total
includes taxes & fees
18 Mar - 19 Mar
The Distinguished Squirrel Chalet walking distance

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 HK$2,069
HK$4,600 total
includes taxes & fees
15 Mar - 16 Mar
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 HK$1,849
HK$4,901 total
includes taxes & fees
15 Mar - 16 Mar
Whiskey Ridge - Luxury Mountaintop Family Retreat * Dog Friendly * Hot Tub

Walk to Trails and Pool, Mtn Views, Shuffleboard, Arcade Fun, Sleeps 10

Walk to Trails and Pool, Mtn Views, Shuffleboard, Arcade Fun, Sleeps 10
Chestnut Springs
10.0 out of 10, Exceptional, (4 reviews)
"Our stay was perfect. The cabin is close to the slopes, but far enough off the main strip that you get the peace and quiet of the mountain. It’s super spacious, with all the amenities you could need. We were only there two nights, but will absolutely be our go to now! "
United States
Lauren W.
The price is HK$1,397
HK$3,377 total
includes taxes & fees
25 Mar - 26 Mar
Walk to Trails and Pool, Mtn Views, Shuffleboard, Arcade Fun, Sleeps 10

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 HK$2,349
HK$6,092 total
includes taxes & fees
15 Mar - 16 Mar
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 HK$2,171
HK$6,833 total
includes taxes & fees
17 Mar - 18 Mar
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

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 HK$4,110
HK$8,167 total
includes taxes & fees
29 Mar - 30 Mar
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

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 HK$3,515
HK$7,956 total
includes taxes & fees
16 Mar - 17 Mar
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 HK$4,110
HK$9,161 total
includes taxes & fees
1 Apr - 2 Apr
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 HK$4,110
HK$8,914 total
includes taxes & fees
29 Mar - 30 Mar
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 HK$704
HK$1,165 total
includes taxes & fees
15 Mar - 16 Mar
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 HK$916
HK$1,585 total
includes taxes & fees
15 Mar - 16 Mar
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, (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 HK$909
HK$1,491 total
includes taxes & fees
15 Mar - 16 Mar
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

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 HK$1,057
HK$1,890 total
includes taxes & fees
15 Mar - 16 Mar
Cozy Country small two bedroom home.

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (50 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is HK$648
HK$896 total
includes taxes & fees
16 Mar - 17 Mar
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
451
Accommodation
197 Vacation Homes
Lowest Price
HK$896
Highest Price
HK$9,161

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