A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Wintergreen vacation rentals

A spacious living area with a wooden staircase, a dining table, and a sofa.

1. Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (6 reviews)
"Cleanliness and ease of check in"
United States
Patrick
The price is NT$5,748
NT$13,776 total
includes taxes & fees
Nov 3 - Nov 4
Blackwood Chalet
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

2. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
The price is NT$4,243
NT$10,256 total
includes taxes & fees
Nov 3 - Nov 4
Three Little Bears
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

3. Panoramic Peak

Panoramic Peak
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (1 review)
"The place was absolutely beautiful and spotless. The view was amazing. The only issue we had was when we asked where it was. We were told Nellysford and didn’t really understand that it was part of the Wintergreen resort so it was much further away from our actual destination. But the place was really amazing. We would stay there again."
United States
Carrie
The price is NT$5,362
NT$9,316 total
includes taxes & fees
Nov 23 - Nov 24
Panoramic Peak
A two-story cabin with a balcony, surrounded by trees.

4. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
The price is NT$9,747
NT$24,674 total
includes taxes & fees
Nov 3 - Nov 4
Blackrock Canopy
Lounge

5. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is NT$6,944
NT$12,374 total
includes taxes & fees
Nov 3 - Nov 4
Firefly on The Ridge
A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.

6. Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
The price is NT$5,748
NT$9,749 total
includes taxes & fees
Nov 22 - Nov 23
Mountain View Vista
A two-story stone house with a deck, outdoor seating, and a fireplace.

7. Red White and Wintergreen

Red White and Wintergreen
2.0 star property
Pedlars Edge
Red White and Wintergreen
A hot tub with a wooden deck and a view of a forest.

8. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is NT$7,098
NT$14,561 total
includes taxes & fees
Nov 16 - Nov 17
Bear Tracks Cottage
A wooden deck with outdoor seating and a fire pit.

9. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is NT$9,644
NT$18,152 total
includes taxes & fees
Nov 9 - Nov 10
Mountain Mindset
Exterior

10. Art & Soul

Art & Soul
2.0 star property
Nellysford
The price is NT$22,819
NT$25,625 total
includes taxes & fees
Nov 16 - Nov 17
Art & Soul
A two-story house with a deck, large windows, and a garage.

11. Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
9.6 out of 10, Exceptional, (28 reviews)
"This place was excellent. Very clean and quiet. Sherando lake was only 4 miles away with great hiking trails. The beds were very comfortable. Would definitely stay at this place again."
United States
Josh
The price is NT$3,736
NT$6,151 total
includes taxes & fees
Dec 1 - Dec 2
Love Ridge Mountain Lodging
A hallway with a wooden staircase, a bench, and a door leading to a balcony.

12. Fore Seasons

Fore Seasons
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (1 review)
"Me and my family had such a great time. The house was clean and beautiful. Everything about the house was amazing. The hosts were very responsive and sincere.❤️"
United States
Menen
The price is NT$5,401
NT$10,458 total
includes taxes & fees
Nov 3 - Nov 4
Fore Seasons
Interior

13. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is NT$8,899
NT$21,190 total
includes taxes & fees
Nov 9 - Nov 10
Modern Nellysford Getaway on 40 Private Acres!
Street view

14. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (278 reviews)
"Clean room convenient parking, good kitchen, friendly staff."
United States
Jamie
The price is NT$3,716
NT$4,136 total
includes taxes & fees
Nov 3 - Nov 4
Valley Extended Suites
An outdoor seating area with a fire pit, wicker chairs, and a view of the landscape.

15. Afton Mountain Vineyards

Afton Mountain Vineyards
3.5 star property
Afton
7.4 out of 10, Good, (3 reviews)
"Cozy and comfortable with pond and mountain views. Wine tasting on site and easy access to Wintergreen. We loved our stay and will be back again!"
United States
Jennifer
The price is NT$11,869
NT$13,329 total
includes taxes & fees
Nov 15 - Nov 16
Afton Mountain Vineyards
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

16. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is NT$4,436
NT$9,558 total
includes taxes & fees
Nov 3 - Nov 4
Bluebird Cottage
A kitchen with green cabinets, a built-in microwave, a coffee maker, and a stove.

17. Enjoy Staunton in the Heart of Shenandoah Valley

Enjoy Staunton in the Heart of Shenandoah Valley
3.0 star property
Staunton
The price is NT$6,357
NT$15,159 total
includes taxes & fees
Nov 3 - Nov 4
Enjoy Staunton in the Heart of Shenandoah Valley
A cabin with a porch, surrounded by trees.

18. Nelson Cozy Cabin

Nelson Cozy Cabin
2.0 star property
Nellysford
The price is NT$7,291
NT$14,594 total
includes taxes & fees
Nov 3 - Nov 4
Nelson Cozy Cabin
A wooden cabin with a stone exterior, a balcony with wooden railings, and outdoor seating with Adirondack chairs.

19. Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is NT$3,858
NT$9,823 total
includes taxes & fees
Nov 3 - Nov 4
Tucked Inn: Lower Unit
A fire pit with chairs, a small house with stairs, and trees in a yard.

20. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is NT$4,590
NT$9,731 total
includes taxes & fees
Nov 3 - Nov 4
Artisan's Cottage
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

Search for holiday rentals in Wintergreen on Expedia! You can easily find your home rentals, villas, holiday apartments in Wintergreen using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Wintergreen?

Yes, there are vacation rentals close to the most popular points of interest in Wintergreen, or you can select a secluded option if you'd like a relaxing place to stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffeehouses during your trip.

How many vacation rentals are there in Wintergreen?

Choose from 232 Expedia vacation rentals in Wintergreen for a memorable vacation.

What can I see and do in Wintergreen?

While you're exploring the area, George Washington National Forest and Humpback Rocks are a couple of picturesque spots to get outside and enjoy nature. While here, Bold Rock Hard Cider Nellysford Cidery and Wintergreen Resort are other places worth a visit.

What’s a vacation rental in Wintergreen like?

A vacation rental is a private property where you can stay for several days or longer in Wintergreen. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.