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Vacation Homes in Wintergreen

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 ¥22,091
¥56,727 total
includes taxes & fees
Aug 29 - Aug 30
Charming 2-bedroom condo in beautiful Wintergreen Resort

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!"
The price is ¥39,763
¥110,146 total
includes taxes & fees
Sep 9 - Sep 10
Spacious 5 bedroom modern home with mountain views galore. Sauna + EV charger.

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

10.0 out of 10, Exceptional, (22)
"The bed was very comfortable and the hot tub was perfect. Enjoyed the views"
The price is ¥13,917
¥44,903 total
includes taxes & fees
Sep 9 - Sep 10
Cozy chalet w/ king beds, fireplace, and hot tub. Dog-friendly! Close to hiking.

The Distinguished Squirrel Chalet walking distance

9.6 out of 10, Exceptional, (5)
"The house was beautiful and well stocked. The owner thought of everything and all the light switches were labeled which helped a lot. All of the appliances were top notch and the Keurig coffee maker had everything that was needed. Beds were very comfortable and each room had its own thermostat. Overall, excellent stay!"
The price is ¥28,753
¥60,701 total
includes taxes & fees
Sep 3 - Sep 4
The Distinguished Squirrel Chalet walking distance

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 ¥44,181
¥94,434 total
includes taxes & fees
Sep 8 - Sep 9
Unwind at Bear Pause, located right at Wintergreen Resort.

Family-Friendly Meets Luxury

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

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

Tucked Inn: Lower Unit - NEW Nelson Co Getaway

2.0 star property
The price is ¥14,727
¥42,174 total
includes taxes & fees
Sep 9 - Sep 10
Tucked Inn: Lower Unit - NEW Nelson Co Getaway

The Firefly Springhouse

10.0 out of 10, Exceptional, (32)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is ¥12,209
¥16,871 total
includes taxes & fees
Aug 31 - Sep 1
The Firefly Springhouse

Waynesboro Home Near Wintergreen Charlottesville

2.0 star property
Waynesboro Home Near Wintergreen Charlottesville

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 ¥15,482
¥43,881 total
includes taxes & fees
Sep 2 - Sep 3
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

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

10.0 out of 10, Exceptional, (2)
"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!"
The price is ¥16,546
¥44,655 total
includes taxes & fees
Sep 1 - Sep 2
Hot Tub | Fire Pit | River | State Park | King Bed

Blue's Barn: Central to Wineries & Breweries

9.4 out of 10, Exceptional, (12)
"Would recommend to anyone who wants a romantic getaway "
Blue's Barn: Central to Wineries & Breweries

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 ¥18,609
¥61,417 total
includes taxes & fees
Sep 1 - Sep 2
Secluded 20+ Acre Retreat Near Brew & Wine Trails

Afton Farmhouse - Mountain Views off Route 151

9.8 out of 10, Exceptional, (24)
"Beautiful location and property!"
The price is ¥23,519
¥65,609 total
includes taxes & fees
Sep 2 - Sep 3
Afton Farmhouse - Mountain Views off Route 151

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 ¥33,725
¥75,747 total
includes taxes & fees
Sep 9 - Sep 10
Fox Hill: 151 Cottage w/Hot Tub + Mountain Views

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 ¥13,536
¥24,092 total
includes taxes & fees
Sep 2 - Sep 3
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Hillside Haven: Modern Retreat, Mountain Views

10.0 out of 10, Exceptional, (28)
"Fantastic property with all the amenities near UVA, and lots of wineries."
The price is ¥26,394
¥61,931 total
includes taxes & fees
Sep 15 - Sep 16
Hillside Haven: Modern Retreat, Mountain Views

Ridgeview Retreat: Mountain Views and Pet Friendly

10.0 out of 10, Exceptional, (10)
"Great property in a great location!"
The price is ¥26,394
¥66,139 total
includes taxes & fees
Sep 9 - Sep 10
Ridgeview Retreat: Mountain Views and Pet Friendly

Little Yellow House: Walk to Downtown Staunton

10.0 out of 10, Exceptional, (5)
"I loved the location and the extra amenities !"
The price is ¥14,598
¥42,114 total
includes taxes & fees
Sep 2 - Sep 3
Little Yellow House: Walk to Downtown Staunton
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

Find out more about Wintergreen

Wintergreen Vacation Homes information

Number of reviews
508
Accommodation
433 Vacation Homes
Lowest Price
¥12,209
Highest Price
¥34,756

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