A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Search Guest Houses in Winchester from CA $256

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Winchester guest houses

Exterior

1. The Goldfinch Suite at Harpers Ferry Guest House

The Goldfinch Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (61 reviews)
"Great location ,Will stay agin."
United States
Kevin L.
The price is CA $239
CA $362 total
includes taxes & fees
Aug 10 - Aug 11
The Goldfinch Suite at Harpers Ferry Guest House
40-inch flat-screen TV with digital channels, Netflix, Hulu

2. The Legacy Inn

The Legacy Inn
3.0 star property
Luray
8.6 out of 10, Excellent, (65 reviews)
"We had a lovely time, the bedrooms all had a beautiful view, and the bathroom clawfoot tub was such fun"
United States
Patricia
The price is CA $100
CA $256 total
includes taxes & fees
Aug 9 - Aug 10
The Legacy Inn
Exterior

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

Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains
10.0 out of 10, Exceptional, (6 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 $345
CA $566 total
includes taxes & fees
Aug 10 - Aug 11
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
Premier Villa, 1 King Bed, Mountain View | Terrace/patio

4. White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (174 reviews)
"Beautiful location with clean rooms and helpful staff. Breakfast and happy hour were a great touch!"
United States
allison
The price is CA $438
CA $472 total
includes taxes & fees
Aug 16 - Aug 17
White Moose Inn
TV, fireplace

5. Riverview Suite at La Soledad

Riverview Suite at La Soledad
Harpers Ferry
10.0 out of 10, Exceptional, (11 reviews)
"Check in/ check out was seamless, nicest place to pick in harper's ferry!"
United States
Brendan P.
The price is CA $351
CA $516 total
includes taxes & fees
Aug 9 - Aug 10
Riverview Suite at La Soledad
Garden

6. Briar Patch Bed & Breakfast Inn

Briar Patch Bed & Breakfast Inn
3.0 star property
Middleburg
7.4 out of 10, Good, (22 reviews)
"It was a beautiful place to stay! My son and I did a quick trip to visit Middleburg and attend the VA hound show. We had to leave early the next morning, and they were wonderful about everything! We are planning to come back and stay longer next time! We loved it there!"
United States
Lindsey
The price is CA $433
CA $494 total
includes taxes & fees
Aug 9 - Aug 10
Briar Patch Bed & Breakfast Inn
Interior

7. The Bluebird Suite at Harpers Ferry Guest House

The Bluebird Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (73 reviews)
"Lovely space. Great location."
United States
Ann H.
The price is CA $239
CA $362 total
includes taxes & fees
Aug 10 - Aug 11
The Bluebird Suite at Harpers Ferry Guest House
Smart TV

8. 2-Room Chickadee Suite @ Harpers Ferry Guest House

2-Room Chickadee Suite @ Harpers Ferry Guest House
Harpers Ferry
9.8 out of 10, Exceptional, (18 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 $275
CA $418 total
includes taxes & fees
Aug 9 - Aug 10
2-Room Chickadee Suite @ Harpers Ferry Guest House
Exterior

9. The Cardinal Suite at Harpers Ferry Guest House

The Cardinal Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (27 reviews)
"Loved the room. The decor was beautiful ! The bed so comfortable!"
United States
Jean Shannon
The price is CA $275
CA $411 total
includes taxes & fees
Aug 12 - Aug 13
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.
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Top Winchester Hotel Reviews

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"We had a quick stay when traveling. Nice stay in a good location to shopping and dining. The room was clean and comfortable, breakfast was available in the morning. Would stay here again."
Bethann 1-night trip
Posted 3 hours ago
Fairfield Inn & Suites by Marriott Winchester

Find out more about Winchester

Winchester Guest Houses information

Number of reviews
430
Accommodation
19 Guest Houses
Lowest Price
CA $256
Highest Price
CA $566

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 $256 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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