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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Sherando holiday rentals

Street view

1. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (263 reviews)
"Would stay again 👍"
United States
Jessica
The price is £87
includes taxes & fees
28 Oct - 29 Oct
Valley Extended Suites
A two-story house with a deck, large windows, and a garage.

2. Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (25 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 £158
includes taxes & fees
5 Nov - 6 Nov
Love Ridge Mountain Lodging
A spacious living area with a wooden staircase, a dining table, and a sofa.

3. 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 £322
includes taxes & fees
8 Oct - 9 Oct
Blackwood Chalet
A bedroom with a large bed, a ceiling fan, and two windows with blinds.

4. 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 £330
includes taxes & fees
12 Oct - 13 Oct
Afton Mountain Vineyards
Interior

5. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is £490
includes taxes & fees
21 Oct - 22 Oct
Modern Nellysford Getaway on 40 Private Acres!
A wooden cabin with a sliding door, a hot tub, and string lights.

6. The Reserve at 151

The Reserve at 151
2.0 star property
Afton
10.0 out of 10, Exceptional, (1 review)
The price is £499
includes taxes & fees
8 Oct - 9 Oct
The Reserve at 151
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

7. 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 £194
includes taxes & fees
2 Nov - 3 Nov
Panoramic Peak
Exterior

8. The Guest Wing at Kateri

The Guest Wing at Kateri
2.0 star property
Waynesboro
10.0 out of 10, Exceptional, (1 review)
"The property was amazing, beyond wonderful. Gracious host. High end furniture and bedding. The backyard and pool area were just beautiful !!! I wish I stayed earlier in the year so i could enjoy the pool. The property is surrounded by wide open farm lands, Starry skies, birds and crickets. It was a very relaxing stay. I wish I could stay longer !!!"
United States
Barbara
The price is £230
includes taxes & fees
2 Nov - 3 Nov
The Guest Wing at Kateri
A fire pit with chairs, a small house with stairs, and trees in a yard.

9. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is £221
includes taxes & fees
3 Nov - 4 Nov
Artisan's Cottage
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

10. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is £203
includes taxes & fees
27 Oct - 28 Oct
Bluebird Cottage
A concrete patio with a wooden bench and a table, surrounded by greenery.

11. Staunton Underground

Staunton Underground
2.0 star property
Staunton
10.0 out of 10, Exceptional, (1 review)
"Charming and well-designed English basement apartment in a perfect central location. It’s in walking distance to the shops and restaurants in charming downtown Staunton. It’s worth pointing out that all descriptions on short-term rental apps says more or less what this one does. This one actually is as described. The furniture is even in good shape! (FWIW, we are really turned off to the just-barely passable rentals we’ve had elsewhere. If all of the rentals delivered like this one, we’d...
United States
BRETT
The price is £160
includes taxes & fees
8 Oct - 9 Oct
Staunton Underground
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

12. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
The price is £220
includes taxes & fees
12 Oct - 13 Oct
Three Little Bears
A modern living room with a large sectional sofa, a fireplace, and a view of the mountains.

13. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is £258
includes taxes & fees
12 Oct - 13 Oct
Firefly on The Ridge
A modern living room with a white sofa, a wooden door, and a ceiling fan.

14. The Wayne Shire

The Wayne Shire
2.0 star property
Waynesboro
The price is £351
includes taxes & fees
8 Oct - 9 Oct
The Wayne Shire
A living room with a brown leather sofa, a grey armchair, a round woven ottoman, a patterned rug, a white table with chairs, and a painting on the wall.

15. Blue Ridge Hideaway

Blue Ridge Hideaway
2.0 star property
Waynesboro
The price is £179
includes taxes & fees
8 Oct - 9 Oct
Blue Ridge Hideaway
A two-story brick building with a white porch and a number '329' sign.

16. Magnolia Suite

Magnolia Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (1 review)
"Great location in small town with some restaurants and shops. The room was spacious and light with high quality interior and design - very nice!!"
Norway
Christian
The price is £150
includes taxes & fees
8 Oct - 9 Oct
Magnolia Suite
A modern kitchen with a large island, dark cabinetry, and a view to the dining area.

17. Little Haven Cottage

Little Haven Cottage
2.0 star property
Afton
8.0 out of 10, Very good, (1 review)
"Good location, very spacious for 4 guests. Excellent choice of LVP flooring instead of carpeting as there was significant rainfall both days of the visit that would have suffered wet shoes on departures and arrivals at the house."
United States
Elizabeth
The price is £312
includes taxes & fees
19 Oct - 20 Oct
Little Haven Cottage
A hot tub with a wooden deck and a view of a forest.

18. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is £313
includes taxes & fees
4 Nov - 5 Nov
Bear Tracks Cottage
A hot tub with a view of a forest and mountains through a window.

19. Fox Hill

Fox Hill
2.0 star property
Afton
The price is £342
includes taxes & fees
2 Nov - 3 Nov
Fox Hill
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.

20. Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
The price is £194
includes taxes & fees
27 Oct - 28 Oct
Mountain View Vista
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 Sherando Hotel Reviews

Hotel 24 South

Hotel 24 South

10/10 Excellent
"Hotel 24 is an amazing gem in part of the country we are unfamiliar with. It was a wonderful surprise after a long day of driving. Nice room, comfortable bed and within walking distance of restaurants and quaint shops. If ever we’re back this way again we would stay again."
Susan 1-night trip
Posted 21 hours ago
Hotel 24 South

Find out more about Sherando

Everything you need to know about Sherando holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sherando holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Sherando holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sherando holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sherando holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sherando holiday rentals we have selected for you start as low as £87 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sherando rentals

At Expedia, we put the best Sherando holiday 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 Sherando 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 Sherando holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sherando. 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 holiday rentals in Sherando?

Yes, there are holiday rentals close to the most popular sights in Sherando, or you can select a more secluded option if you're looking for a relaxing stay. Sherando is known for its parks.

What are some of the best holiday rentals that Sherando has to offer?

Wintergreen cabin, hot tub, sauna, walk to trails: This holiday home rental outside of Sherando is located in the mountains, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What’s there to see and do in Sherando?

Explore the area and family-friendly sights such as Sunspots Studios Glassblowing, or get out into nature at a spot like George Washington National Forest. In the wider area, you’ll find Humpback Rocks and Raven's Roost Overlook.

What’s a holiday rental in Sherando like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sherando. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.