Sherando Vacation Rentals from $127: 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.

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Our top choices for Sherando vacation rentals

1. Valley Extended Suites

Fishersville

Jamie

$114 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

2. Love Ridge Mountain Lodging

Lyndhurst

Josh

$186 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

Rebecca B.

$153 nightly

Nov 16 - Nov 17

Total with taxes and fees

A covered porch with a wooden railing, a stone bench, and two chairs with cushions.

4. The Serendipity Suite

Staunton

Jennifer

$175 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

5. The Firefly Springhouse

Staunton

David H

$93 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

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

Waynesboro

Elisa G.

$156 nightly

Nov 9 - Nov 10

Total with taxes and fees

A two-story house with a front porch, a mailbox, and a wooden fence.

7. 2 minutes from the shops and activities; Cozy 1 bedroom end unit.

Wintergreen

Joseph Blaine

$200 nightly

Nov 8 - Nov 9

Total with taxes and fees

A garden with a variety of flowers and trees at dusk.

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

Roseland

Kathleen K.

$214 nightly

Nov 12 - Nov 13

Total with taxes and fees

A spacious living area with a wooden ceiling, a sofa, a coffee table, and a kitchen in the background.

9. Rockwell Ridge | Inn with Afton Mountain Views

Afton

$354 nightly

Nov 15 - Nov 16

Total with taxes and fees

A balcony with a table and chairs, offering a view of a mountainous landscape.

10. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Roseland

michael b.

$211 nightly

Nov 9 - Nov 10

Total with taxes and fees

A set of stone steps leading up to a house with a light-colored exterior.

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

Wintergreen Resort

Jennifer D.

$213 nightly

Nov 11 - Nov 12

Total with taxes and fees

A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

12. Updated! Cozy and clean two bedroom condo.

Wintergreen Resort

Joel M.

$209 nightly

Nov 12 - Nov 13

Total with taxes and fees

A two-story wooden cabin with a wooden deck and a small porch.

13. Walk to Market/Private community outdoor pool!

Wintergreen Resort

Christy P.

$209 nightly

Nov 12 - Nov 13

Total with taxes and fees

A log cabin with a covered porch, surrounded by a gravel path and dense greenery.

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

Roseland

Anna W.

$173 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wooden deck with wicker furniture, a brick wall, and a view of greenery.

15. Bluebird Cottage

Roseland

$261 nightly

Nov 10 - Nov 11

Total with taxes and fees

A small cabin with a porch, surrounded by trees.

16. Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Montebello

Jake

$179 nightly

Nov 8 - Nov 9

Total with taxes and fees

An outdoor dining area with wicker chairs, a table with plates and glasses, a fire pit, and a barbecue grill.

17. Secluded 20+ Acre Retreat Near Brew & Wine Trails

Afton

Phyllis A.

$328 nightly

Nov 8 - Nov 9

Total with taxes and fees

A log cabin with a red door, a welcome sign, and a window with a hanging flower arrangement.

18. Willow Haven: Cozy cabin in delightful Afton

Afton

Travis W.

$206 nightly

Nov 9 - Nov 10

Total with taxes and fees

A hot tub with a control panel, surrounded by a backyard with trees and a house in the background.

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

Waynesboro

Kathleen

$168 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

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

Wintergreen Resort

Sang Rea

$264 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Top Sherando Hotel Reviews

Sleep Inn Staunton

8/10 Good

"La location est parfaite, tout près de la 81. La salle de bain est petite, ce qui rend l utilisatio de la douche plus difficile d accès."

Spark by Hilton Staunton

8/10 Good

"The hotel was nice, but I do have some comments… my hotel room bathroom was very dirty in the shower - it seems like the cleaner only spot cleaned and were were many places where the shower was not cleaned well. The reason I didn’t say anything was because I was only staying one night and didn’t see a point, so I used my flip flops in the shower. The hotel was nice, but I was very alarmed at the noisy elevator which often jumped and left me very concerned."

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 $127 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.

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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 Serendipity Suite

5. The Firefly Springhouse

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

7. 2 minutes from the shops and activities; Cozy 1 bedroom end unit.

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

9. Rockwell Ridge | Inn with Afton Mountain Views

10. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

12. Updated! Cozy and clean two bedroom condo.

13. Walk to Market/Private community outdoor pool!

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

15. Bluebird Cottage

16. Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

17. Secluded 20+ Acre Retreat Near Brew & Wine Trails

18. Willow Haven: Cozy cabin in delightful Afton

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

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

Find vacation rentals that suit your style

Top Sherando Hotel Reviews

Sleep Inn Staunton

Holiday Inn Express & Suites Staunton by IHG

Grey Pine Lodge

Spark by Hilton Staunton

Love Ridge Mountain Lodging

Clarion Pointe Staunton East

Holiday Inn Staunton Conference Center by IHG

Find out more about Sherando

Frequently asked questions

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