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Sherando Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Sherando holiday rentals

A compact kitchen with a stove, a dining area with chairs and a table, and a small seating area with a sofa and a lamp.

1. Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.0 out of 10, Wonderful, (70 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is AU$155
includes taxes & fees
6 Oct - 7 Oct
Affordable Suites of America Waynesboro

2. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (258 reviews)
"Would stay again 👍"
United States
Jessica
The price is AU$166
includes taxes & fees
7 Oct - 8 Oct
Valley Extended Suites
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

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

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (59 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
The price is AU$636
includes taxes & fees
28 Sept - 29 Sept
Spacious + Serene Mtn Top Escape, 4 En Suites
A room with a wooden floor, a table with two stools, and a view through large windows with blinds.

4. Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (36 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
The price is AU$317
includes taxes & fees
27 Sept - 28 Sept
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.

5. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (60 reviews)
"Nice resort"
United States
Diana J.
The price is AU$264
includes taxes & fees
28 Sept - 29 Sept
Where the Trail Ends
A garden with a variety of flowers and trees at dusk.

6. 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, (161 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 AU$353
includes taxes & fees
27 Sept - 28 Sept
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A house with a white exterior, a window with a hanging plant, and a garden with hydrangea flowers.

7. 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, (24 reviews)
"Owner was communicative. Lots of space. Decor was unique."
United States
Clement
The price is AU$265
includes taxes & fees
27 Sept - 28 Sept
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
A mountainous landscape with dense green forests and a clear sky.

8. 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, (333 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 AU$341
includes taxes & fees
27 Sept - 28 Sept
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
An outdoor dining area with wicker chairs, a table with plates and glasses, a fire pit, and a barbecue grill.

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

Secluded 20+ Acre Retreat Near Brew & Wine Trails
Afton
9.8 out of 10, Exceptional, (26 reviews)
"Everything was exactly as stated. We loved the house and the close proximity to the 151. We will definitely come back! "
United States
Harold R.
Secluded 20+ Acre Retreat Near Brew & Wine Trails
A wooden deck with a round table and chairs, overlooking a grassy area with trees.

10. 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, (129 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is AU$359
includes taxes & fees
27 Sept - 28 Sept
Escape to the Blue Ridge Mountains at Wine-tergreen!
A two-story house with a deck, large windows, and a garage.

11. Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (24 reviews)
"This place was excellent. Very clean and quiet. Sherando lake was only 4 miles away with great hiking trails. The beds were very comfortable. Would definitely stay at this place again."
United States
Josh
The price is AU$313
includes taxes & fees
30 Sept - 1 Oct
Love Ridge Mountain Lodging
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.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (36 reviews)
"Great stay for my family!"
United States
Joel M.
The price is AU$362
includes taxes & fees
28 Sept - 29 Sept
Updated! Cozy and clean two bedroom condo.
A two-story house with a stone foundation, a large front porch, and a chimney.

13. 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, (123 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
The price is AU$415
includes taxes & fees
29 Sept - 30 Sept
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
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.

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

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.6 out of 10, Exceptional, (21 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
The price is AU$244
includes taxes & fees
7 Oct - 8 Oct
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

15. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is AU$379
includes taxes & fees
28 Sept - 29 Sept
Bluebird Cottage

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

"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
Wintergreen Resort
10.0 out of 10, Exceptional, (43 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
United States
Amy K.
The price is AU$434
includes taxes & fees
27 Sept - 28 Sept
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A house with a covered patio, sliding glass doors, and a small outdoor seating area with chairs.

17. Mountain Retreat in Wintergreen!

Mountain Retreat in Wintergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
The price is AU$398
includes taxes & fees
4 Oct - 5 Oct
Mountain Retreat in Wintergreen!
An outdoor seating area with wooden chairs and a central fire pit, surrounded by a stone wall and a building with a red roof.

18. The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (35 reviews)
"Well supplied with essentials , charming"
United States
Beth
The price is AU$451
includes taxes & fees
27 Sept - 28 Sept
The Cottage @ Afton Mountain- Close to Wineries!
A bedroom with a large bed, a dresser, and a ceiling fan. There are two windows providing a view of the outdoors.

19. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (15 reviews)
"Relaxing, scenic, quiet during the week, clean, modern, great communication with the host."
United States
Darlene
The price is AU$408
includes taxes & fees
27 Sept - 28 Sept
Mountain View Vista: Resort Condo w/ Views
A stone staircase leading to a wooden house with a door and a poster on the wall.

20. The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (72 reviews)
"Nice stay. Perfect for the solo traveler"
United States
David H
The price is AU$164
includes taxes & fees
28 Sept - 29 Sept
The Firefly Springhouse
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

Spark by Hilton Waynesboro

Spark by Hilton Waynesboro

8/10 Good
"The property was recently refurbished and done well. My room was clean though it could have been scrubbed a bit better in the bathroom. The AC unit worked but I believe the unit should have been replaced. All in all a good stay."
Lisa 1-night trip
Posted 10 hours ago
Spark by Hilton Waynesboro

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$166 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.