Wintergreen Vacation Rentals

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Check prices for these dates

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

Our top choices for Wintergreen holiday 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 RM714
RM1,711 total
includes taxes & fees
9 Nov - 10 Nov
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 RM527
RM1,274 total
includes taxes & fees
8 Nov - 9 Nov
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 RM709
RM1,206 total
includes taxes & fees
24 Nov - 25 Nov
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 RM1,575
RM3,474 total
includes taxes & fees
6 Dec - 7 Dec
Blackrock Canopy
Lounge

5. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is RM863
RM1,537 total
includes taxes & fees
24 Nov - 25 Nov
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 RM714
RM1,211 total
includes taxes & fees
15 Nov - 16 Nov
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 RM880
RM1,809 total
includes taxes & fees
16 Nov - 17 Nov
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 RM1,216
RM2,278 total
includes taxes & fees
9 Nov - 10 Nov
Mountain Mindset
Exterior

10. Art & Soul

Art & Soul
2.0 star property
Nellysford
The price is RM3,047
RM3,421 total
includes taxes & fees
19 Nov - 20 Nov
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, (30 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 RM464
RM764 total
includes taxes & fees
7 Dec - 8 Dec
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 RM772
RM1,412 total
includes taxes & fees
7 Dec - 8 Dec
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 RM1,105
RM2,632 total
includes taxes & fees
9 Nov - 10 Nov
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, (279 reviews)
"Clean room convenient parking, good kitchen, friendly staff."
United States
Jamie
The price is RM462
RM514 total
includes taxes & fees
8 Nov - 9 Nov
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 RM1,474
RM1,656 total
includes taxes & fees
15 Nov - 16 Nov
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 RM553
RM1,191 total
includes taxes & fees
15 Nov - 16 Nov
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 RM790
RM1,883 total
includes taxes & fees
8 Nov - 9 Nov
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 RM906
RM1,813 total
includes taxes & fees
17 Nov - 18 Nov
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 RM479
RM1,220 total
includes taxes & fees
8 Nov - 9 Nov
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 RM572
RM1,213 total
includes taxes & fees
9 Nov - 10 Nov
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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Find out more about Wintergreen

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

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Look no further and take a look at our great range of rental properties in Wintergreen!

Frequently Asked Questions

Can I find holiday rentals in Wintergreen?

Yes, there are holiday rentals close to the most popular sights in Wintergreen, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffee shops during your trip.

How many holiday rentals are there in Wintergreen?

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

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 holiday rental in Wintergreen like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wintergreen. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family getaway.