Sherando Vacation Rentals from $127: Search Short-Term Rentals

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Our top choices for Sherando vacation rentals

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

Roseland

Michelle

$219 nightly

Sep 6 - Sep 7

Total with taxes and fees

Standard Suite, 1 Queen Bed | Private kitchen

2. Affordable Suites of America Waynesboro

Waynesboro

Frank

$119 nightly

Sep 30 - Oct 1

Total with taxes and fees

3. Where the Trail Ends

Wintergreen Resort

Diana J.

$156 nightly

Sep 9 - Sep 10

Total with taxes and fees

4. Valley Extended Suites

Fishersville

Kate

$114 nightly

Sep 6 - Sep 7

Total with taxes and fees

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

Roseland

Deborah R.

$190 nightly

Sep 7 - Sep 8

Total with taxes and fees

6. Blair's Vintage Apartment Nestled in Wine Country

Waynesboro

George S.

$203 nightly

Sep 6 - Sep 7

Total with taxes and fees

Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Terrace/patio

7. Love Ridge Mountain Lodging

Lyndhurst

Josh

$207 nightly

Sep 13 - Sep 14

Total with taxes and fees

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

Wintergreen Resort

Jennifer D.

$229 nightly

Sep 8 - Sep 9

Total with taxes and fees

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Top Sherando Hotel Reviews

Holiday Inn Express & Suites Waynesboro East by IHG

10/10 Excellent

"We greatly appreciated getting a room with two queen beds and a pullout sofa bed, given the size of her family, and given that we only booked it the same day. Very appreciative of the staff and also enjoyed their buffet breakfast. We would highly recommend this hotel."

avid hotel Staunton by IHG

8/10 Good

"We loved the Staff and the hotel overall-- very helpful for any extras ( needed a few more bath towels for our extra long weekend stay). The breakfast was excellent ( delish and abundant choices) and the beverages were available day and night. Loved the tile floors in the rooms, the carpeted hallways kept the other areas quiet. Fast elevators. It is a pet friendly hotel and was kept very clean outside too, with complimentary dog treats at the front desk area. Pool was a good temperature, just no lounge chairs in there. Overall, we enjoyed our stay and would definitely recommend this hotel again. Other mentions-- the restaurant just down the hill ( we walked there) was great too! Very friendly and good food at very reasonable prices. A Cracker Barrel was across the roadway and a hill and they were good too. We did have trouble with Uber and Lyft drivers --they are not very available or reliable in the Staunton area. We did eventually find one driver who we used for a few rides ( without the app) who was very reliable and at a reasonable cost. We did not have a vehicle (came in by train to the valley)."

Clarion Pointe Staunton East

10/10 Excellent

"Beautiful views, clean rooms, friendly staff, nice luggage carts, nice pool, plenty of parking. The only thing I would have liked that wasn't available was more light over the desk and food areas in the room and an extra plug at the food area for the coffee pot. We will definitely stay here again!"

Comfort Inn & Suites Staunton

10/10 Excellent

"This was a much better stay than the Comfort Inn in Cleveland that we stayed at just a few nights before. The hotel needs a renovation but they did the best they could with that they had. It was very clean, well maintained and the staff was great. The breakfast room was stocked, well equipped and clean."

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?

Berry Hill Lake - Private Luxury Family Resort w/ Pool & Hot Tub - Pet Friendly: This vacation home rental near Sherando is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Afton Mountain Vineyards.

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

2. Affordable Suites of America Waynesboro

3. Where the Trail Ends

4. Valley Extended Suites

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

6. Blair's Vintage Apartment Nestled in Wine Country

7. Love Ridge Mountain Lodging

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

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

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

11. First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

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

13. Panoramic Peak: Wintergreen Condo with Views

14. Updated! Cozy and clean two bedroom condo.

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

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

17. Mountain Retreat in Wintergreen!

18. Shenandoah Valley Atelier: NEW Waynesboro Loft

19. Wintergreen Condo -Steps to Ski and restaurants

20. Mountain View Vista: Resort Condo w/ Views

Find vacation rentals that suit your style

Top Sherando Hotel Reviews

Holiday Inn Express & Suites Waynesboro East by IHG

Sleep Inn Staunton

Howard Johnson by Wyndham Staunton

Hotel 24 South

Tru By Hilton Staunton

avid hotel Staunton by IHG

Clarion Pointe Staunton East

The Blackburn Inn and Conference Center

Comfort Inn & Suites Staunton

Find out more about Sherando

Frequently asked questions

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