Sherando Vacation Rentals from $109: Search Short-Term Rentals

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Sherando vacation rentals

1. Valley Extended Suites

Fishersville

michael

$98 nightly

Nov 2 - Nov 3

Total with taxes and fees

A two-story house with a deck, large windows, and a garage.

2. Love Ridge Mountain Lodging

Lyndhurst

Josh

$182 nightly

Nov 18 - Nov 19

Total with taxes and fees

A rustic wooden cabin with a sign reading "Rusty's Retreat." It features large windows, a door, and is surrounded by a garden with plants and a large tree.

3. Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Afton

Caitlin S.

$153 nightly

Oct 21 - Oct 22

Total with taxes and fees

A house with a white exterior, a window with a hanging plant, and a garden with hydrangea flowers.

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

Waynesboro

Elisa G.

$168 nightly

Oct 21 - Oct 22

Total with taxes and fees

A room with a brown leather sofa, a wooden bench, and a window with curtains.

5. Rockwell Ridge | Inn with Afton Mountain Views

Afton

$347 nightly

Nov 3 - Nov 4

Total with taxes and fees

A stone staircase leading to a wooden house with a door and a poster on the wall.

6. The Firefly Springhouse

Staunton

David H

$103 nightly

Oct 21 - Oct 22

Total with taxes and fees

A wooden deck with a round table and chairs, overlooking a grassy area with trees.

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

Wintergreen Resort

Jennifer D.

$230 nightly

Oct 20 - Oct 21

Total with taxes and fees

A mountainous landscape with dense green forests and a clear sky.

8. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Roseland

Virginia

$224 nightly

Oct 25 - Oct 26

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Sherando Hotel Reviews

Spark by Hilton Waynesboro

10/10 Excellent

"Room was clean. Comfortable bed."

Spark by Hilton Staunton

10/10 Excellent

"The room was spacious, very clean and updated. The bed and bedding were so soft and comfortable we didn’t want to get up. The continental breakfast had hot options and a yogurt machine with toppings bar. All staff we encountered were very friendly and helpful! I will recommend this Spark Hotel to everyone!"

Grey Pine Lodge

8/10 Good

"Room was clean other than several of granddaddy long legs just hanging around the place, especially the bathroom. I could not get the access code for the hotel shop to work, and I tried multiple times with the instructions given. Not a huge deal, but a little inconvenient. I don’t think I was alone in that struggle because I didn’t see anyone go in there during my stay. Price was kind steep for what you get, but accommodations in the area are limited so supply and demand I guess. I would stay here again though, location is honestly 10/10 and stones throw to Shenandoah and the Blue Ridge Parkway."

Sleep Inn Staunton

8/10 Good

"The hotel lived up to its name as the bed was pretty comfortable and I fell asleep quick. Room has everything you need by bathroom is narrow and if you are a big person I can see where this may be a problem. Otherwise the breakfast was very decent but mostly your basics. Only real complaint was room did smell a bit musty like old water damage and I could see if your sensitive to this it could be a problem. We basically only slept in the room and were so tired every day after initial smell you kind of stopped noticing lol. Would stay here again if price is right overall. Room seemed clean and updated overall. About 10 min to downtown Staunton."

Find out more about Sherando

Everything you need to know about Sherando 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 Sherando 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 Sherando vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sherando vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sherando 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 $109 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 Sherando rentals

At Expedia, we put the best Sherando 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 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 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 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 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.

Room 1

Check prices for these dates

Our top choices for Sherando vacation rentals

1. Valley Extended Suites

2. Love Ridge Mountain Lodging

3. Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

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

5. Rockwell Ridge | Inn with Afton Mountain Views

6. The Firefly Springhouse

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

8. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9. Willow Haven: Cozy cabin in delightful Afton

10. The Bons Amis Suite

11. Updated! Cozy and clean two bedroom condo.

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

13. Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

14. Walk to Market/Private community outdoor pool!

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

16. NEW! Cheerful 2 bd bungalow with hot tub. Must see!

17. "Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

18. Afton Cottage w/ Hot Tub, Firepit, Mountain Views

19. Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC

20. Bluebird Cottage

Find vacation rentals that suit your style

Top Sherando Hotel Reviews

Spark by Hilton Waynesboro

Hotel 24 South

Spark by Hilton Staunton

Holiday Inn Express & Suites Waynesboro East by IHG

Days Inn by Wyndham Staunton

Holiday Inn Staunton Conference Center by IHG

Grey Pine Lodge

Sleep Inn Staunton

The Blackburn Inn and Conference Center

Find out more about Sherando

Frequently asked questions