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Sherando Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

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, (252 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is AED 419
AED 466 total
includes taxes & fees
23 Aug - 24 Aug
Valley Extended Suites
Exterior

2. Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
10.0 out of 10, Exceptional, (122 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
The price is AED 446
AED 1,000 total
includes taxes & fees
20 Aug - 21 Aug
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Property grounds

3. Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (119 reviews)
"Gorgeous views! We spent most of our time out and about, but enjoyed our stay!"
United States
Jennifer P.
The price is AED 518
AED 1,179 total
includes taxes & fees
27 Aug - 28 Aug
Endless Mountain Top Views from All The Way Up!
Property grounds

4. New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (159 reviews)
"We had a calm and relaxing mountain get a way. The property was charming and perfect for us, clean and organized. The location was great. We loved to go for walks nearby and visit the gnomes and fairies in the trees. We would love to make it an annual trip and would definitely stay here again."
United States
Michelle
The price is AED 404
AED 912 total
includes taxes & fees
20 Aug - 21 Aug
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
House, Private Bathroom (Fox Hill) | Outdoor spa tub

5. Fox Hill

Fox Hill
2.0 star property
Afton
The price is AED 841
AED 1,666 total
includes taxes & fees
23 Aug - 24 Aug
Fox Hill
Outdoor dining

6. Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (128 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is AED 426
AED 949 total
includes taxes & fees
20 Aug - 21 Aug
Escape to the Blue Ridge Mountains at Wine-tergreen!
1 bedroom, in-room safe, iron/ironing board, WiFi (free)

7. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (14 reviews)
"Relaxing, scenic, quiet during the week, clean, modern, great communication with the host."
United States
Darlene
The price is AED 665
AED 1,270 total
includes taxes & fees
17 Sep - 18 Sep
Mountain View Vista: Resort Condo w/ Views
Smart TV, fireplace, table tennis, books

8. 4 BR cabin mins to trails & breweries pets welcome

4 BR cabin mins to trails & breweries pets welcome
Chestnut Springs
9.6 out of 10, Exceptional, (35 reviews)
"We really enjoyed our stay in Wintergreen! The location was great and the view was incredible. The house was spotless and we loved that there was a full kitchen. We recommend to others! "
United States
Laura J.
The price is AED 711
AED 2,180 total
includes taxes & fees
20 Aug - 21 Aug
4 BR cabin mins to trails & breweries pets welcome
Property grounds

9. Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16

Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16
Deer Springs
10.0 out of 10, Exceptional, (11 reviews)
"It's a nice house, and check in/out was super easy."
United States
Chris R.
The price is AED 1,180
AED 2,944 total
includes taxes & fees
23 Aug - 24 Aug
Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16
Interior

10. Elk Mountain Overlook: Breathtaking Views

Elk Mountain Overlook: Breathtaking Views
Afton
9.0 out of 10, Wonderful, (8 reviews)
"Well equipped Cabin with amazing views"
United States
Margaret
The price is AED 841
AED 1,718 total
includes taxes & fees
27 Aug - 28 Aug
Elk Mountain Overlook: Breathtaking Views
Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Terrace/patio

11. Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (22 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is AED 470
AED 748 total
includes taxes & fees
17 Sep - 18 Sep
Love Ridge Mountain Lodging
A mountainous landscape with dense green forests and a clear sky.

12. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (330 reviews)
"Our 2-BR condo was lovely. Everything was sparkling clean and the place was spacious for what we needed. What MADE it, though, was the VIEW which was spectacular! I felt we should have been pre-informed that there was no coffee for us to use. We could have easily brought some but didn’t know of its non-existence."
United States
Virginia
The price is AED 433
AED 1,002 total
includes taxes & fees
17 Sep - 18 Sep
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Coffee/tea maker, fridge, microwave, oven

13. Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (39 reviews)
"We had an incredible stay this past week. The condo "
United States
Holly M.
The price is AED 598
AED 1,509 total
includes taxes & fees
20 Aug - 21 Aug
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Coffee/tea maker, fridge, microwave, oven

14. Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Wintergreen Resort
10.0 out of 10, Exceptional, (42 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is AED 380
AED 1,149 total
includes taxes & fees
20 Aug - 21 Aug
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Cabin, Private Bathroom (Blackwood Chalet) | Lounge

15. Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (5 reviews)
"Love the area"
United States
Toni
The price is AED 621
AED 1,522 total
includes taxes & fees
20 Aug - 21 Aug
Blackwood Chalet
Property grounds

16. Luxury Condo in the Sky! Finest in Wintergreen!

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (40 reviews)
"Very clean and nicely supplied and decorated. Wonderful views from the living room! Planning on going back to this property again. "
United States
Charlie B.
The price is AED 500
AED 1,159 total
includes taxes & fees
24 Aug - 25 Aug
Luxury Condo in the Sky! Finest in Wintergreen!
Smart TV, fireplace, books

17. Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (56 reviews)
"Great place"
United States
Stephen M.
The price is AED 443
AED 1,512 total
includes taxes & fees
23 Aug - 24 Aug
Spacious + Serene Mtn Top Escape, 4 En Suites
Terrace/patio

18. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay for our family of 4 for a wedding weekend. Easy check-in and close to the Inn."
United States
Scott M.
The price is AED 429
AED 993 total
includes taxes & fees
26 Aug - 27 Aug
Wintergreen Condo -Steps to Ski and restaurants
TV, fireplace, offices

19. The Branch at Afton Mountain Retreat

The Branch at Afton Mountain Retreat
Afton
10.0 out of 10, Exceptional, (38 reviews)
"We loved our 2 night stay at this absolutely perfect property ! The place was decorated so tastefully and was immaculate and clean. Beds were super comfortable and bathrooms were modern and updated. The shower had great water pressure and we especially enjoyed having our morning coffee on the lovely screened in porch. Perfect location for wineries and breweries and a short drive to Charlottesville/UVA. We will definitely return and highly recommend! "
United States
Denise M.
The price is AED 753
AED 1,631 total
includes taxes & fees
23 Aug - 24 Aug
The Branch at Afton Mountain Retreat
Exterior detail

20. The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Waynesboro
10.0 out of 10, Exceptional, (22 reviews)
"Great host and beautifully decorated property."
United States
Elisa G.
The price is AED 413
AED 689 total
includes taxes & fees
23 Aug - 24 Aug
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
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

avid hotel Staunton by IHG

avid hotel Staunton by IHG

10/10 Excellent
"Avid is excellent hotel with plenty of parking, neat rooms with two queen beds, and neat bath room. Very good breakfast, Highly recommend."
Venkateswar 1-night trip
Posted 15 hours ago
avid hotel Staunton by IHG

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?

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14: This vacation home near Sherando is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 War Fields, or get out into nature at a spot like George Washington National Forest. In the larger area, you’ll find Afton Mountain Vineyards and Blue Ridge Parkway North Entrance.

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.