Search Guest Houses in Winchester from CA $81

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Check prices for these dates

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. 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)
"Room was perfect for our 2 night stay"
United States
Diane J.
The price is CA $207
CA $311 total
includes taxes & fees
Nov 23 - Nov 24
The Bluebird Suite at Harpers Ferry Guest House

3. White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (188 reviews)
"Wonderful stay, a very roomy, yet cozy place, with great character."
United States
Blake
The price is CA $431
CA $465 total
includes taxes & fees
Dec 6 - Dec 7
White Moose Inn

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 $343
CA $392 total
includes taxes & fees
Dec 1 - Dec 2
Briar Patch Bed & Breakfast Inn

5. Romantic Barn Loft | Wine Country & Weddings

Romantic Barn Loft | Wine Country & Weddings
Paeonian Springs
The price is CA $216
CA $350 total
includes taxes & fees
Dec 1 - Dec 2
Romantic Barn Loft | Wine Country & Weddings

6. 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 $207
CA $309 total
includes taxes & fees
Nov 9 - Nov 10
The Goldfinch Suite at Harpers Ferry Guest House

7. 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 $347
CA $544 total
includes taxes & fees
Nov 19 - Nov 20
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

8. 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 $223
CA $337 total
includes taxes & fees
Nov 9 - Nov 10
2-Room Chickadee Suite @ Harpers Ferry Guest House

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 $437
CA $583 total
includes taxes & fees
Nov 15 - Nov 16
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 $223
CA $331 total
includes taxes & fees
Nov 19 - Nov 20
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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