Sherando Holiday Rentals: Short-Term Accommodations for Rent

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

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 : This holiday home rental outside of Sherando is located in the mountains, and has a fireplace, a patio and a BBQ 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 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. Affordable Suites of America Waynesboro

Waynesboro

Frank

HK$690 total

includes taxes & fees

12 Aug - 13 Aug

2. Valley Extended Suites

Fishersville

Kate

HK$995 total

includes taxes & fees

10 Aug - 11 Aug

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

Roseland

Michelle

HK$1,947 total

includes taxes & fees

10 Aug - 11 Aug

4. Love Ridge Mountain Lodging

Lyndhurst

Timika

HK$1,603 total

includes taxes & fees

7 Sept - 8 Sept

5. Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen Resort

Sebastian A.

HK$2,313 total

includes taxes & fees

10 Aug - 11 Aug

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

Wintergreen Resort

Jennifer D.

HK$2,027 total

includes taxes & fees

10 Aug - 11 Aug

7. Where the Trail Ends

Wintergreen Resort

April S.

HK$1,603 total

includes taxes & fees

18 Aug - 19 Aug

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

Waynesboro

Elisa G.

HK$1,471 total

includes taxes & fees

10 Aug - 11 Aug

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Top Sherando Hotel Reviews

The Blackburn Inn and Conference Center

10/10 Excellent

"Beautiful grounds, well-kept rooms and a 10 minute stroll to town. You do need a walk signal across the road howecer; during the day, crossing the street is a challenge. In the evening, though, no problem."

Hotel 24 South

10/10 Excellent

"A Beautiful Property in the Heart of Downtown Hotel 24 South is an outstanding property in a fantastic downtown location. From the moment we arrived, the staff was friendly, welcoming, and genuinely helpful. The service added a personal touch that made the stay especially enjoyable. The hotel itself is beautiful, well-maintained, and full of character. Being right in the heart of downtown makes it incredibly convenient for exploring the area, with restaurants, shops, and attractions all within easy reach. Overall, Hotel 24 South delivers a wonderful combination of location, atmosphere, and hospitality. A very enjoyable stay and an easy four-star recommendation. With just a few small touches, it could easily move into five-star territory."

Howard Johnson by Wyndham Staunton

8/10 Good

"The biggest advantage of this hotel is that it's 5-10 min. walking distance from downtown and Mary Baldwin University and that it is less expensive than other nearby hotels. Room was of a decent size. It had microwave, small fridge, iron and ironing board, hair dryer which which was very useful. It also had a coffee maker, but I didn't use it. The only downside was that, although it was labeled as a non-smoking room and it was written that it has been serviced to be such a room, every time you would walk into the room from outside, it would smell like a smoker's room. The hotel has a washer and dryer coins operated, another useful feature if you stay longer. Staff was wonderful. My nephew turned 10 during our stay and tha staff bought him birthday cake, card and present. Breakfast was decent: cereals, waffles, bagels, toast, butter, peanuts butter, cream cheese, jam, oatmeal, juice, coffee, tea, apples, bananas... My nephew and I loved the most "Swiss Miss" chocolate powder and we enjoyed hot chocolate every morning. There was plenty of parking space in front of the hotel. Considering everything, I will definitely stay there again if I come to Staunton."

Holiday Inn Express & Suites Staunton by IHG

8/10 Good

"The room, upon arrival, looked like it was made up by a toddler; not what one would expect even from a Motel 6. One of the elevators was out; things happen but was par for the course for the stay. Most irritating, however, was the charge for parking. We're not talking about New York City here. We're talking about the outskirts of Staunton; there is NOTHING around....and yet, charge for parking? I could park ANYWHERE in downtown Staunton for free! All in all, lost me for good. FAR better options are everywhere."

Best Western Plus Waynesboro Inn & Suites Conference Center

8/10 Good

"Stayed for a quick overnight. Staff was very friendly. Breakfast provided good options. Pool was closed for renovations. Hotel was updated in most areas, however still some outdated features such as the bathtub. Convenient to restaurants and the major highways."

Find out more about Sherando

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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?

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14: This holiday home rental outside of Sherando is located in the mountains, and has a fireplace, a patio and a BBQ 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 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 War Fields, or get out into nature at a spot like George Washington National Forest. In the wider area, you’ll find Humpback Rocks and Afton Mountain Vineyards.

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.

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Check prices for these dates

Our top choices for Sherando holiday rentals

1. Affordable Suites of America Waynesboro

2. Valley Extended Suites

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

4. Love Ridge Mountain Lodging

5. Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

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

7. Where the Trail Ends

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

9. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

11. Endless Mountain Top Views from All The Way Up!

12. Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

13. Blair's Vintage Apartment Nestled in Wine Country

14. Mountain View Vista: Resort Condo w/ Views

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

16. Panoramic Peak: Wintergreen Condo with Views

17. Mountain Retreat in Wintergreen!

18. Willow Haven: Cozy cabin in delightful Afton

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

20. little mountain haven. True ski-in Ski out

Find holiday rentals that suit your style

Top Sherando Hotel Reviews

The Blackburn Inn and Conference Center

Hotel 24 South

Howard Johnson by Wyndham Staunton

Holiday Inn Express & Suites Waynesboro East by IHG

Clarion Pointe Staunton East

Holiday Inn Express & Suites Staunton by IHG

Quality Inn Verona - Staunton North

Sleep Inn Staunton

Best Western Plus Waynesboro Inn & Suites Conference Center

Find out more about Sherando

Frequently asked questions

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