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Sherando Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Sherando vacation rentals

Street view

1. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (260 reviews)
"Would stay again 👍"
United States
Jessica
The price is AED 381
AED 424 total
includes taxes & fees
3 Nov - 4 Nov
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 AED 539
AED 826 total
includes taxes & fees
6 Oct - 7 Oct
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 AED 657
AED 1,563 total
includes taxes & fees
4 Oct - 5 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 AED 1,433
AED 1,609 total
includes taxes & fees
4 Oct - 5 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 AED 1,003
AED 2,388 total
includes taxes & fees
6 Oct - 7 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 AED 896
AED 2,244 total
includes taxes & fees
5 Oct - 6 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 AED 525
AED 961 total
includes taxes & fees
3 Nov - 4 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 AED 753
AED 1,145 total
includes taxes & fees
7 Oct - 8 Oct
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 AED 437
AED 1,006 total
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 AED 422
AED 990 total
includes taxes & fees
5 Oct - 6 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 AED 327
AED 778 total
includes taxes & fees
4 Oct - 5 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 AED 404
AED 1,072 total
includes taxes & fees
4 Oct - 5 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 AED 661
AED 1,258 total
includes taxes & fees
4 Oct - 5 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 AED 621
AED 1,713 total
includes taxes & fees
4 Oct - 5 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 AED 404
AED 858 total
includes taxes & fees
26 Oct - 27 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 AED 378
AED 732 total
includes taxes & fees
4 Oct - 5 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
The price is AED 621
AED 1,522 total
includes taxes & fees
5 Oct - 6 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 AED 694
AED 1,522 total
includes taxes & fees
4 Oct - 5 Oct
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 AED 841
AED 1,666 total
includes taxes & fees
5 Oct - 6 Oct
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 AED 511
AED 945 total
includes taxes & fees
4 Oct - 5 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

Spark by Hilton Waynesboro

Spark by Hilton Waynesboro

10/10 Excellent
"It was nice, new and Clean!"
William 1-night trip
Posted 2 hours ago
Spark by Hilton Waynesboro

Frequently asked questions

Can I find vacation rentals in Sherando?

Yes, we have vacation rentals close to well known points of interest in Sherando, or you can select a secluded option if you're looking for relaxation. Sherando is known for its parks.

What are some of the best vacation rentals in Sherando?

Wintergreen cabin, hot tub, sauna, walk to trails: This vacation home rental near Sherando 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.

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 larger area, you’ll find Humpback Rocks and Raven's Roost Overlook.

What’s a vacation rental in Sherando like?

A vacation rental is a private property you can stay in for a couple of days or more in Sherando. Vacation rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.