Search Guest Houses in Winchester from CA $81

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Our top choices for Winchester guest houses

1. The Legacy Inn

The Legacy Inn
3.0 star property
Luray
8.4 out of 10, Very good, (71 reviews)
"The place is super clean and the manager is so friendly! I only put a 4 for the amenities because the vent in our bathroom really doesn’t dry the moisture unless we leave the door open. We would definitely stay here again."
United States
Rosalinda
The price is CA $81
CA $236 total
includes taxes & fees
Nov 9 - Nov 10
The Legacy Inn

2. White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (189 reviews)
"Wonderful stay at White Moose Lodge. Great staff, clean, well-appointed rooms, and a delicious breakfast. We will definitely be back."
United States
Jennifer
The price is CA $386
CA $416 total
includes taxes & fees
Dec 9 - Dec 10
White Moose Inn

3. The Bluebird Suite at Harpers Ferry Guest House

The Bluebird Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (77 reviews)
"Wonderful suite in a perfect location - walk to lower town. The room was clean and spacious, with a beautiful bathroom and a nice sized mini-fridge. The hosts left snacks, yogurt, cereal and milk. Coffee maker with pods, creamer and sugar. Great stay for a long weekend - highly recommend!!"
United States
Danielle
The price is CA $208
CA $311 total
includes taxes & fees
Nov 9 - Nov 10
The Bluebird Suite at Harpers Ferry Guest House

4. Briar Patch Bed & Breakfast Inn

Briar Patch Bed & Breakfast Inn
3.0 star property
Middleburg
7.0 out of 10, Good, (26 reviews)
"Beautiful property"
United States
Phyllis
The price is CA $346
CA $395 total
includes taxes & fees
Dec 1 - Dec 2
Briar Patch Bed & Breakfast Inn

5. The Goldfinch Suite at Harpers Ferry Guest House

The Goldfinch Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (65 reviews)
"Very much enjoyed our stay and recommend it."
United States
Robert A.
The price is CA $208
CA $311 total
includes taxes & fees
Nov 9 - Nov 10
The Goldfinch Suite at Harpers Ferry Guest House

6. Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
9.0 out of 10, Wonderful, (7 reviews)
"This was a great place to escape to! Very quiet and peaceful but close to some great restaurants and vineyards."
United States
Jill M.
The price is CA $350
CA $548 total
includes taxes & fees
Nov 12 - Nov 13
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

7. 2-Room Chickadee Suite @ Harpers Ferry Guest House

2-Room Chickadee Suite @ Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (24 reviews)
"The homey, comfortable atmosphere and the location are stand-outs of this charming, B&B. Great hosts!"
United States
Jason
The price is CA $225
CA $340 total
includes taxes & fees
Nov 9 - Nov 10
2-Room Chickadee Suite @ Harpers Ferry Guest House

8. Romantic Barn Loft | Wine Country & Weddings

Romantic Barn Loft | Wine Country & Weddings
Paeonian Springs
The price is CA $218
CA $353 total
includes taxes & fees
Nov 16 - Nov 17
Romantic Barn Loft | Wine Country & Weddings

9. Riverview Suite at La Soledad

Riverview Suite at La Soledad
Harpers Ferry
9.8 out of 10, Exceptional, (15 reviews)
"Check in/ check out was seamless, nicest place to pick in harper's ferry!"
United States
Brendan P.
The price is CA $441
CA $587 total
includes taxes & fees
Nov 12 - Nov 13
Riverview Suite at La Soledad

10. The Cardinal Suite at Harpers Ferry Guest House

The Cardinal Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (30 reviews)
"Everything was exceptional, very quiet and good location. We really appreciated the EV charging!"
United States
Sue K.
The price is CA $225
CA $332 total
includes taxes & fees
Nov 10 - Nov 11
The Cardinal Suite at Harpers Ferry Guest House
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.

Winchester and related destinations

Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theatre.

A white neoclassical building with columns, an American flag, and a clock tower.

Frequently Asked Questions

What is the nightly rate for a guest house in Winchester?

Rates for Winchester guest houses vary, but travelers can find great-value prices from CA $81 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Winchester guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.

What's the difference between a Winchester guest house and a B&B?

A guest house in Winchester is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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