Holiday Homes in Wintergreen

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Wintergreen holiday homes

Exterior

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)
"House was clean and comfortable. The hot tub was nice and also clean."
United States
William K.
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Smart TV, fireplace, ping pong, books

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, (34 reviews)
"WE HAD A WONDERFUL TIME. WE HAD EVERYTHING WE NEEDED. HOUSE WAS BEAUTIFUL, COMFORTABLE AND COZY!!"
Canada
Janet C.
The price is €501
includes taxes & fees
3 Jun - 4 Jun
4 BR cabin mins to trails & breweries pets welcome
Smart TV, fireplace, books

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 €461
includes taxes & fees
3 Jun - 4 Jun
Beautiful 4-season Mountain Home- New Listing
Smart TV, fireplace, books

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)
"We had a wonderful stay, everything was just as described. I would definitely stay again"
United States
kevin M.
Spacious + Serene Mtn Top Escape, 4 En Suites
Dining

"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.
"Glass & Pine" Home close to Bold Rock & Vineyards
TV, fireplace, offices

The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance
Treeloft
9.0 out of 10, Wonderful, (12 reviews)
"This was one of the most well-stocked houses we've ever rented. The owners thought of everything. The house was very comfortable for our group. Access to the Tyro ski slope was 4 houses down, so no need to drive anyone to the slope. The view was beautiful - we would absolutely stay here again!"
United States
Carrie G.
The Distinguished Squirrel Chalet walking distance
Terrace/patio

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

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.
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
Terrace/patio

Mountain Retreat: Year-Round Getaway, Pup Friendly

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
Mountain Retreat: Year-Round Getaway, Pup Friendly
Outdoor spa tub

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

Red White & WTG: Game Room + Hot Tub

Red White & WTG: Game Room + Hot Tub
Pedlars Edge
10.0 out of 10, Exceptional, (8 reviews)
"House was perfection. Very comfortable beds and every comfort of home is available in this property. Perfect place for two families of four to enjoy a fun weekend on the mountain. "
United States
Kate T.
The price is €880
includes taxes & fees
3 Jun - 4 Jun
Red White & WTG: Game Room + Hot Tub
Outdoor spa tub

Stunning Views, Hot Tub, Impeccable Design

Stunning Views, Hot Tub, Impeccable Design
Wintergreen Resort
10.0 out of 10, Exceptional, (15 reviews)
"This house is beautiful, well kept, and is in a great location near hikes and breweries!"
United States
Lauren M.
Stunning Views, Hot Tub, Impeccable Design
Smart TV, fireplace

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 €630
includes taxes & fees
7 Jun - 8 Jun
7th Hole Chalet - Summer Getaway w Hot Tub, Sauna
Room

Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is €441
includes taxes & fees
3 Jun - 4 Jun
Mountain Mindset
Exterior detail

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 €164
includes taxes & fees
3 Jun - 4 Jun
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Interior

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"House was perfect for overnight stay. 30 min from Vines Center and easy to find."
United States
Unspecified U.
The price is €132
includes taxes & fees
4 Jun - 5 Jun
Whole House
Shower, hair dryer, towels, soap

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (65 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 €102
includes taxes & fees
8 Jun - 9 Jun
The Firefly Springhouse
Outdoor spa tub

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, (56 reviews)
"Perfect for what we needed. "
United States
Matt & Jean
The price is €179
includes taxes & fees
8 Jun - 9 Jun
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Outdoor dining

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (16 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is €256
includes taxes & fees
3 Jun - 4 Jun
Historic Bungalow 30 minutes from Wintergreen
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

Where the Trail Ends

Where the Trail Ends

10/10 Excellent
"Very nice condo. Great location. Clean. Comfortable."
Aline L. 1-night trip
Posted 3 days ago
Where the Trail Ends

Find out more about Wintergreen

Wintergreen Holiday Homes information

Number of reviews
394
Accommodation
193 Holiday Homes
Lowest Price
€102
Highest Price
€880