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 $257

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Winchester guest houses

A kitchen with a coffee maker, a refrigerator, and a countertop.

1. The Bluebird Suite at Harpers Ferry Guest House

The Bluebird Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (75 reviews)
"Room was perfect for our 2 night stay"
United States
Diane J.
The price is CA $240
CA $366 total
includes taxes & fees
Sep 23 - Sep 24
The Bluebird Suite at Harpers Ferry Guest House
A room with a marble table, a bookshelf, a sofa, and a wooden console table.

2. The Legacy Inn

The Legacy Inn
3.0 star property
Luray
8.4 out of 10, Very good, (67 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 $101
CA $257 total
includes taxes & fees
Sep 23 - Sep 24
The Legacy Inn
A two-story building with a garage entrance, surrounded by lush greenery and a stone wall.

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 $346
CA $568 total
includes taxes & fees
Sep 24 - Sep 25
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
A spacious living room with a high ceiling, built-in bench seating, a coffee table, and large windows offering a view of the outdoors.

4. Riverview Suite at La Soledad

Riverview Suite at La Soledad
Harpers Ferry
10.0 out of 10, Exceptional, (12 reviews)
"Check in/ check out was seamless, nicest place to pick in harper's ferry!"
United States
Brendan P.
The price is CA $404
CA $583 total
includes taxes & fees
Sep 23 - Sep 24
Riverview Suite at La Soledad
A lush garden with a variety of plants and trees, a small stream, and a wooden fence in the background.

5. Briar Patch Bed & Breakfast Inn

Briar Patch Bed & Breakfast Inn
3.0 star property
Middleburg
7.0 out of 10, Good, (25 reviews)
"Beautiful property"
United States
Phyllis
The price is CA $424
CA $484 total
includes taxes & fees
Sep 23 - Sep 24
Briar Patch Bed & Breakfast Inn
An open doorway leading to a room with a dining table and chairs, a sofa, and a window.

6. White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (182 reviews)
"Wonderful stay, a very roomy, yet cozy place, with great character."
United States
Blake
The price is CA $406
CA $437 total
includes taxes & fees
Sep 27 - Sep 28
White Moose Inn
A rustic outdoor seating area with Adirondack chairs, a fire pit, and a wooden table.

7. Romantic Barn Loft | Wine Country & Weddings

Romantic Barn Loft | Wine Country & Weddings
Paeonian Springs
The price is CA $232
CA $383 total
includes taxes & fees
Sep 23 - Sep 24
Romantic Barn Loft | Wine Country & Weddings
A two-story white building with a porch, a sign reading "Harper's Guest House," and a flag.

8. The Goldfinch Suite at Harpers Ferry Guest House

The Goldfinch Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (63 reviews)
"Very much enjoyed our stay and recommend it."
United States
Robert A.
The price is CA $239
CA $363 total
includes taxes & fees
Oct 7 - Oct 8
The Goldfinch Suite at Harpers Ferry Guest House
A two-story white building with a porch, a sign reading "Harper's Guest House," and a flag.

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, (29 reviews)
"Loved the room. The decor was beautiful ! The bed so comfortable!"
United States
Jean Shannon
The price is CA $277
CA $411 total
includes taxes & fees
Sep 23 - Sep 24
The Cardinal Suite at Harpers Ferry Guest House
A cozy living room with a grey sofa, a coffee table, and a wooden door leading to another room.

10. 2-Room Chickadee Suite @ Harpers Ferry Guest House

2-Room Chickadee Suite @ Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (22 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 $277
CA $421 total
includes taxes & fees
Sep 23 - Sep 24
2-Room Chickadee Suite @ 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

Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"Location was very convenient and included inside access to 24hr Denny’s. Parking lot adjacent to an Exxon. Hot breakfast, hard boiled eggs, English"
Joanne 1-night trip
Posted less than an hour ago
Quality Inn Winchester

Find out more about Winchester

Winchester Guest Houses information

Number of reviews
406
Accommodation
16 Guest Houses
Lowest Price
CA $257
Highest Price
CA $583

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 $257 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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