Holiday Homes in Wintergreen

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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, (54 reviews)
"The place was very clean and spacious. The communication from the hosts was helpful. We had a very pleasant stay."
United States
James S.
The price is AU$493
includes taxes & fees
19 Apr - 20 Apr
Spacious + Serene Mtn Top Escape, 4 En Suites

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, (31 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 AU$453
includes taxes & fees
29 Apr - 30 Apr
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

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)
"Beautiful place. Exactly as depicted in the listing. Very responsive host with questions prior to my stay."
United States
Philip S.
The price is AU$830
includes taxes & fees
22 Apr - 23 Apr
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 AU$570
includes taxes & fees
29 Apr - 30 Apr
"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)
"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 AU$761
includes taxes & fees
22 Apr - 23 Apr
Beautiful 4-season Mountain Home- New Listing

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 AU$675
includes taxes & fees
22 Apr - 23 Apr
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 AU$634
includes taxes & fees
29 Apr - 30 Apr
Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin

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 AU$1,095
includes taxes & fees
5 May - 6 May
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 AU$1,410
includes taxes & fees
22 Apr - 23 Apr
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

Red White & WTG: Game Room + Hot Tub

Red White & WTG: Game Room + Hot Tub
Pedlars Edge
10.0 out of 10, Exceptional, (8 reviews)
"I liked the following: -spacious house -supplies on hand -cleanliness of the house -location -quietness -# of bathrooms and bedrooms -no pets rule -no smoking rule -house decor"
United States
Deran
Red White & WTG: Game Room + Hot Tub

Mountain Retreat: Year-Round Getaway, Pup Friendly

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is AU$778
includes taxes & fees
29 Apr - 30 Apr
Mountain Retreat: Year-Round Getaway, Pup Friendly

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Everything was great. "
United States
Nathan T.
The price is AU$210
includes taxes & fees
19 Apr - 20 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 AU$263
includes taxes & fees
22 Apr - 23 Apr
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)
"Wonderful property within a short drive to the resort for snowboarding. Had everything you would need f9"
United States
Melissa R.
The price is AU$348
includes taxes & fees
20 Apr - 21 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 AU$414
includes taxes & fees
17 Apr - 18 Apr
Historic Bungalow 30 minutes from Wintergreen

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (56 reviews)
"The room was very clean and conveniently located for us."
United States
Jeanell S.
The price is AU$162
includes taxes & fees
27 Apr - 28 Apr
The Firefly Springhouse

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (33 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 AU$582
includes taxes & fees
22 Apr - 23 Apr
Hillside Haven: Modern Retreat, Mountain Views

Secluded 20+ Acre Retreat Near Brew & Wine Trails

Secluded 20+ Acre Retreat Near Brew & Wine Trails
Afton
10.0 out of 10, Exceptional, (13 reviews)
"Everything was exactly as stated. We loved the house and the close proximity to the 151. We will definitely come back! "
United States
Harold R.
The price is AU$484
includes taxes & fees
19 Apr - 20 Apr
Secluded 20+ Acre Retreat Near Brew & Wine Trails

Fox Hill: Hot Tub, Views, Pet Friendly!

Fox Hill: Hot Tub, Views, Pet Friendly!
Afton
10.0 out of 10, Exceptional, (15 reviews)
"Everything was perfect. We needed a night away and this was the perfect place to end up."
United States
Dave D.
The price is AU$725
includes taxes & fees
22 Apr - 23 Apr
Fox Hill: Hot Tub, Views, Pet Friendly!

Tucked Inn: Lower Unit - NEW Nelson Co Getaway

Tucked Inn: Lower Unit - NEW Nelson Co Getaway
Nellysford
The price is AU$410
includes taxes & fees
22 Apr - 23 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
366
Accommodation
196 Holiday Homes
Lowest Price
AU$162
Highest Price
AU$1,410