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
$376 nightly
The price is $423
Nov 9 - Nov 10
Total with taxes and fees
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
$280 nightly
The price is $315
Nov 8 - Nov 9
Total with taxes and fees
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
$265 nightly
The price is $298
Nov 24 - Nov 25
Total with taxes and fees
Panoramic Peak
A two-story cabin with a balcony, surrounded by trees.

4. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
$683 nightly
The price is $767
Nov 17 - Nov 18
Total with taxes and fees
Blackrock Canopy
Lounge

5. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
$338 nightly
The price is $380
Nov 24 - Nov 25
Total with taxes and fees
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
$266 nightly
The price is $299
Nov 15 - Nov 16
Total with taxes and fees
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
$397 nightly
The price is $445
Nov 16 - Nov 17
Total with taxes and fees
Bear Tracks Cottage
A wooden deck with outdoor seating and a fire pit.

9. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
$499 nightly
The price is $561
Nov 9 - Nov 10
Total with taxes and fees
Mountain Mindset
Exterior

10. Art & Soul

Art & Soul
2.0 star property
Nellysford
$700 nightly
The price is $786
Nov 8 - Nov 9
Total with taxes and fees
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, (29 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
$186 nightly
The price is $202
Nov 18 - Nov 19
Total with taxes and fees
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
$286 nightly
The price is $321
Nov 8 - Nov 9
Total with taxes and fees
Fore Seasons
Interior

13. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
$579 nightly
The price is $650
Nov 9 - Nov 10
Total with taxes and fees
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
$114 nightly
The price is $127
Nov 8 - Nov 9
Total with taxes and fees
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
$405 nightly
The price is $454
Nov 15 - Nov 16
Total with taxes and fees
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
$261 nightly
The price is $293
Nov 15 - Nov 16
Total with taxes and fees
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
$415 nightly
The price is $465
Nov 8 - Nov 9
Total with taxes and fees
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
$399 nightly
The price is $448
Nov 9 - Nov 10
Total with taxes and fees
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
$268 nightly
The price is $301
Nov 16 - Nov 17
Total with taxes and fees
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
$266 nightly
The price is $299
Nov 9 - Nov 10
Total with taxes and fees
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

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

Blackwood Chalet

Blackwood Chalet
Nellysford

10/10 Excellent

Cleanliness and ease of check in
United States
Patrick
Reviewed September 13, 2026
Blackwood Chalet

Find out more about Wintergreen

Everything you need to know about Wintergreen vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wintergreen vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wintergreen vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wintergreen. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wintergreen in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $230 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wintergreen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wintergreen vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wintergreen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

What are some of the best vacation rentals that Wintergreen has to offer?

Wintergreen cabin, hot tub, sauna, walk to trails: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Wintergreen are Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 and Remodeled 3BR/2BA Ski Chalet off Tyro Slope.

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.

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