Sherando, VA Vacation Homes from AED 420

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Our top choices for Sherando vacation homes

A hotel room with a bed, a nightstand with a lamp, a blue tissue box, and a window with a curtain.

1. Rockwell Ridge | Inn with Afton Mountain Views

Afton

AED 1,442 total

includes taxes & fees

3 Nov - 4 Nov

A house with a white exterior, a window with a hanging plant, and a garden with hydrangea flowers.

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

Waynesboro

Elisa G.

AED 740 total

includes taxes & fees

25 Oct - 26 Oct

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

3. The Firefly Springhouse

Staunton

David H

AED 420 total

includes taxes & fees

12 Oct - 13 Oct

An outdoor dining area with wicker chairs, a table with plates and glasses, a fire pit, and a barbecue grill.

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

Afton

Harold R.

A wooden cabin with a stone exterior, a balcony with wooden railings, and outdoor seating with Adirondack chairs.

5. Tucked Inn: Lower Unit

Nellysford

AED 1,031 total

includes taxes & fees

12 Oct - 13 Oct

A dining area with a wooden table and chairs, a chandelier, and a view of the outdoors through a window.

6. Rockwell Ridge | Private Retreat w/ Mountain Views

Afton

AED 2,791 total

includes taxes & fees

3 Nov - 4 Nov

7. Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!

Waynesboro

Cameron V.

AED 1,877 total

includes taxes & fees

12 Oct - 13 Oct

A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

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

Wintergreen Resort

Maija

AED 1,451 total

includes taxes & fees

8 Oct - 9 Oct

A hot tub with a control panel, surrounded by a backyard with trees and a house in the background.

9. NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Waynesboro

Sally A.

AED 809 total

includes taxes & fees

25 Oct - 26 Oct

A circular fire pit with a metal rim and a flat top, surrounded by a stone border.

10. Rockwell Ridge | Chestnut Suite with Lux Bathroom

Afton

"This property was spotlessly clean, carefully and well furnished, with clear instructions about everything. The location was peaceful and quiet, and we were treated to seeing a doe and young fawn not long after arriving. With no traffic or other noise, we had a restful stay.The host's communications were welcoming and comprehensive.While off the main roads, it is still convenient to attractions and amenities in Waynesboro. This is a perfect place to unwind; with several more rooms on the...

Peter & Stephanie R.

AED 805 total

includes taxes & fees

3 Nov - 4 Nov

A circular stone fire pit with two Adirondack chairs around it, set on a gravel surface.

11. Peaceful Retreat w/ Hot Tub, Fire Pit, Mountain Views

Afton

Amber

AED 1,859 total

includes taxes & fees

14 Oct - 15 Oct

A cabin with a large window, surrounded by trees.

12. Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Wintergreen Resort

Stanley W.

AED 1,385 total

includes taxes & fees

13 Oct - 14 Oct

A cozy living room with wooden paneling, a fireplace, a grey sofa, and a round coffee table.

13. Afton Farmhouse - Mountain Views off Route 151

Afton

Traci S.

AED 1,842 total

includes taxes & fees

3 Nov - 4 Nov

A wooden deck with a blue planter table holding a yellow flower pot.

14. Historic Bungalow 30 minutes from Wintergreen

Roseland

Scott P.

AED 1,013 total

includes taxes & fees

15 Oct - 16 Oct

A modern kitchen with white cabinets, a central island with stools, stainless steel appliances, and pendant lighting.

15. Afton Farmhouse

Afton

AED 1,134 total

includes taxes & fees

12 Oct - 13 Oct

16. Charming Vacation Rental in a Barn on a Horse Farm near Afton Mountain in Virginia

Afton

Shannon P.

A covered patio with a round table and chairs, a sofa, and a view of a grassy yard through large windows.

17. Rosé All Day: Wine Country Getaway! Walk to Dining

Crozet

Sam B.

A lush garden with a variety of plants and trees, a well-maintained lawn, and a distant mountain range under a partly cloudy sky.

18. Amazing Mountain Views, Hot Tub and Close to Wineries and Breweries

Afton

Catherine S.

AED 1,659 total

includes taxes & fees

14 Oct - 15 Oct

A laundry room with two stacked washing machines and a drying machine.

19. Little Yellow House: Walk to Downtown Staunton

Staunton

Miriam

A spacious kitchen with a central island, a dining area with a table and chairs, and a black leather sofa.

20. Blue Ridge Beau, Lost In The View

Afton

Michael V.

AED 2,020 total

includes taxes & fees

19 Oct - 20 Oct

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Top Sherando Hotel Reviews

Hotel 24 South

10/10 Excellent

"Hotel 24 is an amazing gem in part of the country we are unfamiliar with. It was a wonderful surprise after a long day of driving. Nice room, comfortable bed and within walking distance of restaurants and quaint shops. If ever we’re back this way again we would stay again."

The Blackburn Inn and Conference Center

8/10 Good

"The hotel is old but beautiful. The floors creak when you walk which adds to the charm. Our only complaint is that there was never any staff available. Checking in took forever because no one was attending the front desk. Every time we went to the front desk, no one was there. Also, every time we called someone, we had to leave a message for a return call. I know they are probably under staffed but it’s not cheap to stay here and it’s frustrating trying to find help."

Days Inn by Wyndham Waynesboro

10/10 Excellent

"I've stayed here at the Days Inn on and off for three years October 2023 to 2026. This is a well main tayed hotel..It's always been very clean and always on time with any nessitity we need. Great location for all kinds of shopping and tourism..Come on down and meet Sam and his family , they're awesome people.. I give Days Inn a 10++++..Rita and Susie 2026 October. 👌👌👌👌 ."

Quality Inn Verona - Staunton North

8/10 Good

"The room was clean and bed was comfortably firm; quiet for being right off the interstate. There's a reason they get high marks on the breakfast too--variety of items, including bite-sized biscuits and gravy & little cheese omelets along with the other items you'd find at a continental breakfast. The exterior would benefit from fresh paint, but overall, very pleased and would stay again if I was in the area."

Room 1

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Check prices for these dates

Our top choices for Sherando vacation homes

1. Rockwell Ridge | Inn with Afton Mountain Views