Sherando Vacation Rentals from CA $101: Short-Term Rentals for 2026

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.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

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

Jamie

CA $179 total

includes taxes & fees

Nov 10 - Nov 11

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

2. Love Ridge Mountain Lodging

Lyndhurst

Josh

CA $252 total

includes taxes & fees

Dec 8 - Dec 9

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.

CA $240 total

includes taxes & fees

Nov 15 - Nov 16

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

4. The Serendipity Suite

Staunton

Jennifer

CA $277 total

includes taxes & fees

Nov 16 - Nov 17

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

5. The Firefly Springhouse

Staunton

David H

CA $149 total

includes taxes & fees

Nov 10 - Nov 11

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.

CA $252 total

includes taxes & fees

Nov 10 - Nov 11

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

CA $321 total

includes taxes & fees

Nov 10 - Nov 11

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.

CA $344 total

includes taxes & fees

Nov 12 - Nov 13

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

CA $572 total

includes taxes & fees

Nov 11 - Nov 12

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.

CA $337 total

includes taxes & fees

Nov 10 - Nov 11

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.

CA $348 total

includes taxes & fees

Nov 11 - Nov 12

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.

CA $336 total

includes taxes & fees

Nov 12 - Nov 13

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.

CA $336 total

includes taxes & fees

Nov 12 - Nov 13

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

Sharon

CA $281 total

includes taxes & fees

Nov 10 - Nov 11

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

15. Bluebird Cottage

Roseland

CA $414 total

includes taxes & fees

Nov 10 - Nov 11

A small cabin with a porch, surrounded by trees.

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

Montebello

Jake

CA $291 total

includes taxes & fees

Nov 10 - Nov 11

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.

CA $538 total

includes taxes & fees

Nov 10 - Nov 11

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.

CA $331 total

includes taxes & fees

Nov 10 - Nov 11

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

CA $264 total

includes taxes & fees

Nov 15 - Nov 16

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

CA $435 total

includes taxes & fees

Nov 10 - Nov 11

View all properties

Find vacation rentals that suit your style

Top Sherando Hotel Reviews

A swimming pool area with four lounge chairs and large windows offering a view of trees.

Hampton Inn Waynesboro/Stuarts Draft

Fishersville

10/10 Excellent

Thomas

A hotel lobby with a reception desk, seating area, and a large window.

Holiday Inn Express & Suites Staunton by IHG

Staunton

10/10 Excellent

Marie-Michele

A clean, modern reception area with a wooden reception desk, a refrigerated display case, and shelves stocked with snacks.

Fairfield Inn & Suites by Marriott Staunton

Staunton

10/10 Excellent

Karen

A snack vending area with various snack options and a beverage dispenser.

Hampton Inn Staunton

Staunton

10/10 Excellent

Hina

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sherando vacation rentals we have selected for you start as low as CA $101 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 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.

Sherando Vacation Rentals

Change your mind

Treat yourself

Be picky

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

Hampton Inn Waynesboro/Stuarts Draft

10/10 Excellent

Find out more about Sherando

Sherando vacation rentals: An excellent choice for every season

How to find incredible deals on Sherando rentals

Frequently Asked Questions

Can I find vacation rentals in Sherando?

What are some of the best vacation rentals in Sherando?

What’s there to see and do in Sherando?

What’s a vacation rental in Sherando like?