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Our top choices for Wintergreen holiday homes

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 £356
includes taxes & fees
6 Apr - 7 Apr
The Distinguished Squirrel Chalet walking distance

Beautiful 4-season Mountain Home- New Listing

Beautiful 4-season Mountain Home- New Listing
Wintergreen Resort
10.0 out of 10, Exceptional, (44 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 £501
includes taxes & fees
12 Apr - 13 Apr
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, (33 reviews)
"Nice place and very clean "
United States
Melad K.
The price is £436
includes taxes & fees
31 Mar - 1 Apr
4 BR cabin mins to trails & breweries pets welcome

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, (29 reviews)
"Well stocked house with great layout for families or two couples. Great kitchen setup with everything you’ll need. Close to the resort and skiing. Close to hiking trails. "
United States
Jeremiah H.
The price is £251
includes taxes & fees
16 Apr - 17 Apr
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (52 reviews)
"Our family enjoyed our staff with the spaciousness of the property and the clean rooms. The kitchen was “Home away from Home”! The host was pleasant and communicative about questions. Thanks for the hospitality! We had a wonderful stay! "
United States
Mike C.
The price is £323
includes taxes & fees
2 Apr - 3 Apr
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 £307
includes taxes & fees
28 Apr - 29 Apr
"Glass & Pine" Home close to Bold Rock & Vineyards

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
Wintergreen Resort
10.0 out of 10, Exceptional, (60 reviews)
"House is beautiful. Questions were answered quickly. Host was proactive about asking if we needed anything. Great experience. "
United States
Brian G.
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

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!
Pedlars Edge
10.0 out of 10, Exceptional, (70 reviews)
"Great stay over Thanksgiving holiday! Home was very cozy with amazing views, wonderful fireplace and hot tub! Also the host was very helpful with wonderful local guide and easy instructions for everything! Would definitely stay here again! "
United States
Phyllis C.
The price is £535
includes taxes & fees
13 Apr - 14 Apr
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

​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, (8 reviews)
"Wonderful house and host! "
United States
Alyshia F.
The price is £812
includes taxes & fees
7 Apr - 8 Apr
​Luxury Oasis! Family&Pets, Outdoor-Lounge, F​ire pit, Hot tub

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
13 Apr - 14 Apr
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 £689
includes taxes & fees
12 Apr - 13 Apr
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly

Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly
Chestnut Springs
10.0 out of 10, Exceptional, (21 reviews)
"Great place for a winter getaway!"
United States
Raven M.
The price is £872
includes taxes & fees
3 Apr - 4 Apr
Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly

Wintergreen Luxury, Breathtaking Views

Wintergreen Luxury, Breathtaking Views
Wintergreen Resort
10.0 out of 10, Exceptional, (6 reviews)
"THE VIEW! Sitting on the deck looking out over the Rockfish Valley is one of the most stunning spots in Virginia."
United States
Henry I.
The price is £1,022
includes taxes & fees
1 Apr - 2 Apr
Wintergreen Luxury, Breathtaking Views

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Everything was great. "
United States
Nathan T.
The price is £115
includes taxes & fees
31 Mar - 1 Apr
Whole House

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 £144
includes taxes & fees
31 Mar - 1 Apr
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, (53 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is £89
includes taxes & fees
31 Mar - 1 Apr
The Firefly Springhouse

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 £187
includes taxes & fees
31 Mar - 1 Apr
Cozy Country small two bedroom home.

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (15 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is £227
includes taxes & fees
31 Mar - 1 Apr
Historic Bungalow 30 minutes from Wintergreen

Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
Nellysford
10.0 out of 10, Exceptional, (7 reviews)
"Adorable, clean and quiet stay! The place was nicer than expected. It's obvious the hosts are thoughtful of their guests - we found everything we needed and more. A short drive into Nellysford and tucked away in the trees. "
United States
Katie K.
The price is £227
includes taxes & fees
31 Mar - 1 Apr
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Tucked Inn: Lower Unit - NEW Nelson Co Getaway

Tucked Inn: Lower Unit - NEW Nelson Co Getaway
Nellysford
The price is £221
includes taxes & fees
6 Apr - 7 Apr
Tucked Inn: Lower Unit - NEW Nelson Co Getaway
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
442
Accommodation
197 Holiday Homes
Lowest Price
£89
Highest Price
£1,022