Photo by Rebecca Brent

Wintergreen Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Wintergreen Vacation Homes

Charming 2-bedroom condo in beautiful Wintergreen Resort
Microwave, oven, stovetop, dishwasher

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 CA $207
CA $526 total
includes taxes & fees
Aug 17 - Aug 18
Charming 2-bedroom condo in beautiful Wintergreen Resort
Cozy chalet w/ king beds, fireplace, and hot tub. Dog-friendly! Close to hiking.
Outdoor spa tub

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"
The price is CA $131
CA $432 total
includes taxes & fees
Aug 25 - Aug 26
Cozy chalet w/ king beds, fireplace, and hot tub. Dog-friendly! Close to hiking.
The Distinguished Squirrel Chalet walking distance
Terrace/patio

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 price is CA $269
CA $570 total
includes taxes & fees
Aug 17 - Aug 18
The Distinguished Squirrel Chalet walking distance
Spacious 5 bedroom modern home with mountain views galore. Sauna + EV charger.
Interior

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 CA $373
CA $1,033 total
includes taxes & fees
Aug 18 - Aug 19
Spacious 5 bedroom modern home with mountain views galore. Sauna + EV charger.
Unwind at Bear Pause, located right at Wintergreen Resort.
Outdoor dining

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 CA $414
CA $886 total
includes taxes & fees
Aug 22 - Aug 23
Unwind at Bear Pause, located right at Wintergreen Resort.
Red White & WTG: Game Room + Hot Tub
Outdoor dining

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."
The price is CA $551
CA $1,313 total
includes taxes & fees
Aug 18 - Aug 19
Red White & WTG: Game Room + Hot Tub
Family-Friendly Meets Luxury
Outdoor dining

Family-Friendly Meets Luxury

9.6 out of 10, Exceptional, (4)
"Plenty of space for multiple families or multiple couples."
The price is CA $1,088
CA $2,020 total
includes taxes & fees
Aug 28 - Aug 29
Family-Friendly Meets Luxury
Tucked Inn: Lower Unit - NEW Nelson Co Getaway
Outdoor dining

Tucked Inn: Lower Unit - NEW Nelson Co Getaway

2.0 star property
The price is CA $138
CA $403 total
includes taxes & fees
Aug 17 - Aug 18
Tucked Inn: Lower Unit - NEW Nelson Co Getaway
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Interior

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 CA $149
CA $251 total
includes taxes & fees
Aug 22 - Aug 23
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
The Firefly Springhouse
Exterior

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 CA $114
CA $158 total
includes taxes & fees
Aug 20 - Aug 21
The Firefly Springhouse
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
Outdoor dining

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 CA $145
CA $411 total
includes taxes & fees
Aug 17 - Aug 18
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
Historic Bungalow 30 minutes from Wintergreen
Exterior

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 CA $129
CA $333 total
includes taxes & fees
Sep 1 - Sep 2
Historic Bungalow 30 minutes from Wintergreen
Spacious Estate on 6 acres, King Suite + Efficiency convenient to I-64 in Crozet
Terrace/patio

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 CA $470
CA $758 total
includes taxes & fees
Aug 17 - Aug 18
Spacious Estate on 6 acres, King Suite + Efficiency convenient to I-64 in Crozet
Blue's Barn: Central to Wineries & Breweries
Pool

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 CA $220
CA $427 total
includes taxes & fees
Aug 17 - Aug 18
Blue's Barn: Central to Wineries & Breweries
Afton Farmhouse - Mountain Views off Route 151
Property grounds

Afton Farmhouse - Mountain Views off Route 151

9.8 out of 10, Exceptional, (23)
"Beautiful location and property!"
The price is CA $221
CA $622 total
includes taxes & fees
Aug 17 - Aug 18
Afton Farmhouse - Mountain Views off Route 151
Pine Creek Tiny House
Outdoor dining

Pine Creek Tiny House

10.0 out of 10, Exceptional, (2)
"The place was clean, comfy and well stocked. We would love to return."
The price is CA $206
CA $346 total
includes taxes & fees
Aug 19 - Aug 20
Pine Creek Tiny House
Secluded 20+ Acre Retreat Near Brew & Wine Trails
Outdoor dining

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"
Secluded 20+ Acre Retreat Near Brew & Wine Trails
Fox Hill: 151 Cottage w/Hot Tub + Mountain Views
Outdoor spa tub

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 CA $261
CA $638 total
includes taxes & fees
Aug 25 - Aug 26
Fox Hill: 151 Cottage w/Hot Tub + Mountain Views
Hot Tub | Fire Pit | River | State Park | King Bed
Fridge, microwave, oven, stovetop

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!"
The price is CA $148
CA $408 total
includes taxes & fees
Aug 28 - Aug 29
Hot Tub | Fire Pit | River | State Park | King Bed
House / hot tub/pet friendly
Outdoor dining

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 CA $230
CA $406 total
includes taxes & fees
Aug 17 - Aug 18
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wintergreen Hotel Reviews

Holiday Inn Express And Suites Waynesboro East by IHG

Holiday Inn Express And Suites Waynesboro East by IHG

10/10 Excellent
"Easy, clean and comfortable. Good breakfast a bonus."
Ryan 1-night trip
Posted 1 day ago
Holiday Inn Express And Suites Waynesboro East by IHG