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Our top choices for Wintergreen holiday homes

"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$1,351
HK$3,193 total
includes taxes & fees
17 Feb - 18 Feb
"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, (25 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$1,297
HK$3,120 total
includes taxes & fees
17 Feb - 18 Feb
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

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)
"Great stay!"
United States
Cheryl P.
The price is HK$1,669
HK$4,089 total
includes taxes & fees
9 Feb - 10 Feb
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, (40 reviews)
"The property is clean, bed rooms are spacious. 3.5 bath, kitchen has latest appliances, bedding & accessories are star hotel standard. We loved our stay. "
United States
Mridul G.
The price is HK$1,552
HK$4,247 total
includes taxes & fees
27 Jan - 28 Jan
Beautiful 4-season Mountain Home- New Listing

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, (10 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$2,251
HK$5,338 total
includes taxes & fees
1 Feb - 2 Feb
Whiskey Ridge - Luxury Mountaintop Family Retreat * Dog Friendly * Hot Tub

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, (29 reviews)
"Nice place and very clean "
United States
Melad K.
The price is HK$2,105
HK$5,367 total
includes taxes & fees
3 Feb - 4 Feb
4 BR cabin mins to trails & breweries pets welcome

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$2,339
HK$6,147 total
includes taxes & fees
2 Feb - 3 Feb
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

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)
"Great stay, clean, comfortable and plenty of room for all. We would rent again. Thanks so much!"
United States
Victoria S.
The price is HK$1,250
HK$3,611 total
includes taxes & fees
26 Jan - 27 Jan
Spacious + Serene Mtn Top Escape, 4 En Suites

The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance
Treeloft
9.0 out of 10, Wonderful, (9 reviews)
"we appreciated that it was stocked with basic spices, coffee, necessary cookware, etc. Nice location "
United States
Ryan R.
The price is HK$2,824
HK$5,452 total
includes taxes & fees
27 Jan - 28 Jan
The Distinguished Squirrel Chalet walking distance

Serene Wintergreen Retreat, Nestled in the Trees

Serene Wintergreen Retreat, Nestled in the Trees
Wintergreen Resort
9.6 out of 10, Exceptional, (18 reviews)
"The property is as wonderful as it looks in the photos. Very close to a beautiful waterfall trail. Definitely would stay here again in a different season to take it all in again."
United States
Brandon D.
The price is HK$2,947
HK$6,418 total
includes taxes & fees
4 Feb - 5 Feb
Serene Wintergreen Retreat, Nestled in the Trees

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$3,416
HK$8,477 total
includes taxes & fees
4 Feb - 5 Feb
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

​Luxury Oasis! Family&Pets, Outdoor-Lounge, F​ire pit, Hot tub

​Luxury Oasis! Family&Pets, Outdoor-Lounge, F​ire pit, Hot tub
Chestnut Springs
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful house and host! "
United States
Alyshia F.
The price is HK$4,093
HK$8,835 total
includes taxes & fees
15 Feb - 16 Feb
​Luxury Oasis! Family&Pets, Outdoor-Lounge, F​ire pit, Hot tub

Family Fun Escape: Hot Tub, Gameroom, Fireplace, Dog Friendly, Firepits & Grill

Family Fun Escape: Hot Tub, Gameroom, Fireplace, Dog Friendly, Firepits & Grill
Chestnut Springs
10.0 out of 10, Exceptional, (15 reviews)
"The house was very clean and a great location for eats and drinks. "
United States
Erin D.
The price is HK$3,388
HK$7,097 total
includes taxes & fees
27 Jan - 28 Jan
Family Fun Escape: Hot Tub, Gameroom, Fireplace, Dog Friendly, Firepits & Grill

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
Treeloft
10.0 out of 10, Exceptional, (68 reviews)
"Loved our stay - the house, location, and amenities were perfect for us!"
United States
Alex & Kathy N.
The price is HK$3,509
HK$6,007 total
includes taxes & fees
5 Feb - 6 Feb
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Mountain Views in Wintergreen

Mountain Views in Wintergreen
Laurel Ridge
10.0 out of 10, Exceptional, (12 reviews)
"Great place for weekend gateaway. "
United States
Brizen R.
Mountain Views in Wintergreen

Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.
Pedlars Edge
9.8 out of 10, Exceptional, (33 reviews)
"The house was great! It was very clean and spacious, and also accessible to older grandparents who use walkers. And the view from the deck is fantastic, particularly with the fall colors. We really enjoyed the activities at Wintergreen, including walking/hiking trails and the riding the chairlift to see fall foliage. We had a great stay! "
United States
Randy S.
The price is HK$3,867
HK$7,310 total
includes taxes & fees
27 Jan - 28 Jan
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

Upscale and Family-Friendly in Wintergreen

Upscale and Family-Friendly in Wintergreen
Roseland
9.6 out of 10, Exceptional, (28 reviews)
"We absolutely loved our stay. Great hiking access point and very family/pet friendly. Would love to come stay again!"
United States
Anonymous traveller
The price is HK$3,684
HK$7,719 total
includes taxes & fees
1 Feb - 2 Feb
Upscale and Family-Friendly in Wintergreen

Trail Magic- Sk-in & Ski-out

Trail Magic- Sk-in & Ski-out
Treeloft
The price is HK$9,263
HK$14,214 total
includes taxes & fees
19 Feb - 20 Feb
Trail Magic- Sk-in & Ski-out

NEW! Cheerful 2 bd bungalow with hot tub. Must see!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.6 out of 10, Exceptional, (45 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
The price is HK$912
HK$1,579 total
includes taxes & fees
28 Jan - 29 Jan
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Whole House

Whole House
Amherst
9.6 out of 10, Exceptional, (35 reviews)
"The property was just what we wanted -- quiet, private, spacious, comfortable, well equipped. Easy to find and everything worked! We will definitely aim to book this property again when we're back in the area."
United States
Andrew
The price is HK$702
HK$1,161 total
includes taxes & fees
26 Jan - 27 Jan
Whole House
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
439
Accommodation
197 Vacation Homes
Lowest Price
HK$1,161
Highest Price
HK$14,214

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