A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

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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, (56 reviews)
"Great place"
United States
Stephen M.
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 £321
includes taxes & fees
7 Jul - 8 Jul
"Glass & Pine" Home close to Bold Rock & Vineyards

Beautiful 4-season Mountain Home- New Listing

Beautiful 4-season Mountain Home- New Listing
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"We had a great time staying here! The place was in great condition and in such a great location! The host was very responsive and helpful with all questions. I would absolutely recommend and will certainly try to book here again in the future!"
United States
Chad H.
The price is £406
includes taxes & fees
30 Jun - 1 Jul
Beautiful 4-season Mountain Home- New Listing

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)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance
Treeloft
9.2 out of 10, Wonderful, (13 reviews)
"Great location and the slopes are easily accessible!"
United States
Mark H.
The price is £318
includes taxes & fees
30 Jun - 1 Jul
The Distinguished Squirrel Chalet walking distance

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
Chestnut Springs
9.8 out of 10, Exceptional, (18 reviews)
"Great stay!"
United States
Cheryl P.
The price is £406
includes taxes & fees
30 Jun - 1 Jul
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

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 £593
includes taxes & fees
30 Jun - 1 Jul
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

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, (35 reviews)
"We really enjoyed our stay in Wintergreen! The location was great and the view was incredible. The house was spotless and we loved that there was a full kitchen. We recommend to others! "
United States
Laura J.
The price is £442
includes taxes & fees
1 Jul - 2 Jul
4 BR cabin mins to trails & breweries pets welcome

Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is £442
includes taxes & fees
30 Jun - 1 Jul
Mountain Mindset

Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds

Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
Laurel Ridge
10.0 out of 10, Exceptional, (5 reviews)
"Fabulous house and we all had a great time! "
United States
Mindy M.
The price is £755
includes taxes & fees
8 Jul - 9 Jul
Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds

7th Hole Chalet - Summer Getaway w Hot Tub, Sauna

7th Hole Chalet - Summer Getaway w Hot Tub, Sauna
Wintergreen Resort
8.0 out of 10, Very good, (1 review)
"We enjoyed our stay at the 7th hole chalet and would return. The house is spacious and was clean and included everything we needed. It did seem to have a lot of extra, unnecessary furniture in some of the rooms and pictures weren't exactly like listing. The landscaping was overgrown and messy out front. There are lots of controls for the heating and air throughout the house, but they are very hard to use and no instructions posted. The hot tub was nice and enjoyed by our crew, but the cover lift...
United States
Paula L.
The price is £652
includes taxes & fees
5 Jul - 6 Jul
7th Hole Chalet - Summer Getaway w Hot Tub, Sauna

Mountain Retreat: Year-Round Getaway, Pup Friendly

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is £500
includes taxes & fees
7 Jul - 8 Jul
Mountain Retreat: Year-Round Getaway, Pup Friendly

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (67 reviews)
"Such a great little place! Quick drive to town, but far enough for a quiet night. Room had everything we needed (and then some) for a short stay, and all the animals were the sweetest added bonus. Would absolutely stay here again if we’re ever back in the area."
United States
Rebekah
The price is £90
includes taxes & fees
30 Jun - 1 Jul
The Firefly Springhouse

Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is £213
includes taxes & fees
30 Jun - 1 Jul
Tucked Inn: Lower Unit

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, (21 reviews)
"Great host and beautifully decorated property."
United States
Elisa G.
The price is £144
includes taxes & fees
6 Jul - 7 Jul
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (38 reviews)
"House was perfect for overnight stay. 30 min from Vines Center and easy to find."
United States
Unspecified U.
The price is £112
includes taxes & fees
7 Jul - 8 Jul
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, (57 reviews)
"This house was a great end to our trip! My kids “loved the vibe” and wished we could have stayed longer. "
United States
Jen T.
The price is £169
includes taxes & fees
14 Jul - 15 Jul
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Rosé All Day: Wine Country Getaway! Walk to Dining

Rosé All Day: Wine Country Getaway! Walk to Dining
Crozet
10.0 out of 10, Exceptional, (26 reviews)
"It was an excellent place to stay while in Crozet. Roomy and nice house."
United States
Carolyn R.
The price is £248
includes taxes & fees
30 Jun - 1 Jul
Rosé All Day: Wine Country Getaway! Walk to Dining

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (36 reviews)
"This was a wonderful, private, modern place to stay! We were here for a visit to Pippin Hill and this was the perfect place!"
United States
Shiloh F.
The price is £314
includes taxes & fees
30 Jun - 1 Jul
Hillside Haven: Modern Retreat, Mountain Views

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 £190
includes taxes & fees
7 Jul - 8 Jul
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 Holiday Homes information

Number of reviews
455
Accommodation
211 Holiday Homes
Lowest Price
£90
Highest Price
£755