Sherando Holiday Rentals from AU$155: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Sherando has to offer?

Wintergreen cabin, hot tub, sauna, walk to trails : This holiday home rental outside of Sherando is located in the mountains, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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Our top choices for Sherando holiday rentals

1. Valley Extended Suites

Fishersville

Jamie

includes taxes & fees

9 Nov - 10 Nov

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

2. Love Ridge Mountain Lodging

Lyndhurst

Josh

includes taxes & fees

8 Dec - 9 Dec

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.

includes taxes & fees

16 Nov - 17 Nov

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

4. The Serendipity Suite

Staunton

Jennifer

includes taxes & fees

16 Nov - 17 Nov

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

5. The Firefly Springhouse

Staunton

David H

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

12 Nov - 13 Nov

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

includes taxes & fees

15 Nov - 16 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

11 Nov - 12 Nov

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.

includes taxes & fees

12 Nov - 13 Nov

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.

includes taxes & fees

12 Nov - 13 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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

15. Bluebird Cottage

Roseland

includes taxes & fees

10 Nov - 11 Nov

A small cabin with a porch, surrounded by trees.

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

Montebello

Jake

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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.

includes taxes & fees

9 Nov - 10 Nov

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

includes taxes & fees

15 Nov - 16 Nov

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

includes taxes & fees

9 Nov - 10 Nov

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Find holiday rentals that suit your style

Find out more about Sherando

Everything you need to know about Sherando holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sherando holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Sherando holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sherando holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sherando holiday rentals we have selected for you start as low as AU$155 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sherando rentals

At Expedia, we put the best Sherando holiday 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 holiday.

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 holiday rentals in Sherando?

Yes, there are holiday rentals close to the most popular sights in Sherando, or you can select a more secluded option if you're looking for a relaxing stay. Sherando is known for its parks.

What are some of the best holiday rentals that Sherando has to offer?

Wintergreen cabin, hot tub, sauna, walk to trails: This holiday home rental outside of Sherando is located in the mountains, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 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 wider area, you’ll find Humpback Rocks and Raven's Roost Overlook.

What’s a holiday rental in Sherando like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sherando. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.

Sherando Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sherando holiday 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 holiday rentals that suit your style

Find out more about Sherando

Sherando holiday rentals: An excellent choice for every season

How to find incredible deals on Sherando rentals

Frequently Asked Questions

Can I find holiday rentals in Sherando?

What are some of the best holiday rentals that Sherando has to offer?

What’s there to see and do in Sherando?

What’s a holiday rental in Sherando like?