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Holiday Homes in Wintergreen

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Featured Holiday Homes in Wintergreen and around

Charming 2-bedroom condo in beautiful Wintergreen Resort

10.0 out of 10, Exceptional, (1)
"We stayed here for a couple of nights over July 4th and it was a nice short getaway. The condo is in a good location - 5 min walk to resort restaurants - and is very comfortable. The kitchen is well-equipped with plenty of cooking tools. The living room seating space was comfortable and allowed for just hanging out. We really enjoyed our stay! "
The price is €335
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom condo in beautiful Wintergreen Resort

Cozy chalet w/ king beds, fireplace, and hot tub. Dog-friendly! Close to hiking.

10.0 out of 10, Exceptional, (21)
"The bed was very comfortable and the hot tub was perfect. Enjoyed the views"
Cozy chalet w/ king beds, fireplace, and hot tub. Dog-friendly! Close to hiking.

The Distinguished Squirrel Chalet walking distance

10.0 out of 10, Exceptional, (4)
"Love the layout, how it was decorated, beds were nice, and every little detail was thought of!"
The Distinguished Squirrel Chalet walking distance

Spacious 5 bedroom modern home with mountain views galore. Sauna + EV charger.

10.0 out of 10, Exceptional, (3)
"We chose this property to celebrate our sons 26th birthday. Cant beat the location, fresh snow at Wintergreen made for great snowboarding. Loved the proximity to local restaurants/breweries. Definitely would recommend!"
Spacious 5 bedroom modern home with mountain views galore. Sauna + EV charger.

Unwind at Bear Pause, located right at Wintergreen Resort.

10.0 out of 10, Exceptional, (1)
"There were a few little hiccups, the top bunk bar was not attached (not an issue as it wasn’t fully needed) and the oven was broken but I message the owner and he replied back very quickly. Neither were an issue for us. The house was perfect! Plenty of cooking supplies for our crew of 12. We loved the deck and spent plenty of time out there and there were more than enough towels for everyone. The check out rules were very clear and reasonable. I would say that something should be listed for the...
The price is €565
includes taxes & fees
22 Aug - 23 Aug
Unwind at Bear Pause, located right at Wintergreen Resort.

Red White & WTG: Game Room + Hot Tub

10.0 out of 10, Exceptional, (3)
"Very clean, check in was so easy and so was checkout! Very close to the slopes. Will stay here again."
Red White & WTG: Game Room + Hot Tub

Family-Friendly Meets Luxury

9.6 out of 10, Exceptional, (4)
"Plenty of space for multiple families or multiple couples."
Family-Friendly Meets Luxury

Tucked Inn: Lower Unit - NEW Nelson Co Getaway

2.0 star property
The price is €257
includes taxes & fees
17 Aug - 18 Aug
Tucked Inn: Lower Unit - NEW Nelson Co Getaway

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

10.0 out of 10, Exceptional, (18)
"Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!"
The price is €160
includes taxes & fees
22 Aug - 23 Aug
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Firefly Springhouse

10.0 out of 10, Exceptional, (31)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is €102
includes taxes & fees
20 Aug - 21 Aug
The Firefly Springhouse

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

10.0 out of 10, Exceptional, (3)
"We had a brief stay but it had all the amenities we needed and was very clean and welcoming. Thank you."
The price is €261
includes taxes & fees
17 Aug - 18 Aug
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Historic Bungalow 30 minutes from Wintergreen

10.0 out of 10, Exceptional, (12)
"I love this place. I’ve stayed there one previous time and it was just as wonderful. Peaceful beautiful home for a relaxing vacation."
The price is €211
includes taxes & fees
1 Sept - 2 Sept
Historic Bungalow 30 minutes from Wintergreen

Spacious Estate on 6 acres, King Suite + Efficiency convenient to I-64 in Crozet

2.0 star property
9.0 out of 10, Wonderful, (2)
"Check in was super convenient and seamless and the house was in a fantastic location with a beautiful sunrise over the road. Hosts were fantastic and hugely supportive when unexpected maintenance issues came up. Very communicative and helpful!"
The price is €483
includes taxes & fees
17 Aug - 18 Aug
Spacious Estate on 6 acres, King Suite + Efficiency convenient to I-64 in Crozet

Blue's Barn: Central to Wineries & Breweries

9.4 out of 10, Exceptional, (12)
"Would recommend to anyone who wants a romantic getaway "
The price is €271
includes taxes & fees
17 Aug - 18 Aug
Blue's Barn: Central to Wineries & Breweries

Afton Farmhouse - Mountain Views off Route 151

9.8 out of 10, Exceptional, (23)
"Beautiful location and property!"
The price is €395
includes taxes & fees
17 Aug - 18 Aug
Afton Farmhouse - Mountain Views off Route 151

Pine Creek Tiny House

10.0 out of 10, Exceptional, (2)
"The place was clean, comfy and well stocked. We would love to return."
Pine Creek Tiny House

Secluded 20+ Acre Retreat Near Brew & Wine Trails

9.8 out of 10, Exceptional, (7)
"The house was clean and very comfortable. Plenty of room for the dog to run around through the woods and for how secluded its only minutes from the distilleries and wineries"
The price is €394
includes taxes & fees
1 Sept - 2 Sept
Secluded 20+ Acre Retreat Near Brew & Wine Trails

Fox Hill: 151 Cottage w/Hot Tub + Mountain Views

10.0 out of 10, Exceptional, (10)
"This property is wonderful for a nice long weekend away in the mountains and wine country. Its proximity to many places on the Nelson 151, and the Blue Ridge Parkway is hard to beat. The hot tub is great as well."
The price is €475
includes taxes & fees
15 Sept - 16 Sept
Fox Hill: 151 Cottage w/Hot Tub + Mountain Views

Hot Tub | Fire Pit | River | State Park | King Bed

10.0 out of 10, Exceptional, (1)
"Such a great place to stay. Had everything you need. Love the theme, made us feel at home. Kids had a blast with the creek and the toys in the kids room. Enjoyed the firepit and the hot tub. Comfy beds. We would love to stay again!"
Hot Tub | Fire Pit | River | State Park | King Bed

House / hot tub/pet friendly

9.8 out of 10, Exceptional, (61)
"Great mountain get-away. Owner was very quick to respond to questions. Good location for hiking and relaxation."
The price is €258
includes taxes & fees
17 Aug - 18 Aug
House / hot tub/pet friendly
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