Search Guest Houses in Winchester from CA $260

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Winchester guest houses

2-Room Chickadee Suite @ Harpers Ferry Guest House

2-Room Chickadee Suite @ Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (14 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 $184
CA $278 total
includes taxes & fees
Mar 3 - Mar 4
2-Room Chickadee Suite @ Harpers Ferry Guest House

Briar Patch Bed & Breakfast Inn

Briar Patch Bed & Breakfast Inn
3.0 star property
Middleburg
8.0 out of 10, Very good, (11 reviews)
"A lovely setting...breakfast was fantastic...cook was charming & everything was tasty & homemade. "
United States
david
Briar Patch Bed & Breakfast Inn

►New! Unique Custom Crafted Train Station Lodge W/ private walking trails

►New! Unique Custom Crafted Train Station Lodge W/ private walking trails
Martinsburg
10.0 out of 10, Exceptional, (22 reviews)
"My friends and I had a great time at the Train Station Lodge! The lodge is a guest house located adjacent to the main house on a large forested property. It was centrally located to the different towns and activities that we wanted to explore, quiet, and a good size for our group. We would totally consider staying here again if we come back to the area! "
United States
Paige H.
The price is CA $117
CA $356 total
includes taxes & fees
Mar 15 - Mar 16
►New! Unique Custom Crafted Train Station Lodge W/ private walking trails

White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (153 reviews)
"Super friendly staff. The hotel is nice, cozy and very clean."
United States
Alejandra
White Moose Inn

Riverview Suite at La Soledad

Riverview Suite at La Soledad
Harpers Ferry
9.8 out of 10, Exceptional, (8 reviews)
"Check in/ check out was seamless, nicest place to pick in harper's ferry!"
United States
Brendan P.
The price is CA $278
CA $424 total
includes taxes & fees
Mar 3 - Mar 4
Riverview Suite at La Soledad

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)
"The hosts are amazing! So accommodating and welcoming. The place is something special. "
United States
AMY B.
The price is CA $338
CA $554 total
includes taxes & fees
Mar 3 - Mar 4
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

The Goldfinch Suite at Harpers Ferry Guest House

The Goldfinch Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (54 reviews)
"Great location ,Will stay agin."
United States
Kevin L.
The price is CA $171
CA $260 total
includes taxes & fees
Mar 3 - Mar 4
The Goldfinch Suite at Harpers Ferry Guest House

The Bluebird Suite at Harpers Ferry Guest House

The Bluebird Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (60 reviews)
"Amazing! Great location to downtown!"
United States
Kimberly J.
The price is CA $171
CA $260 total
includes taxes & fees
Mar 3 - Mar 4
The Bluebird Suite at Harpers Ferry Guest House

The Cardinal Suite at Harpers Ferry Guest House

The Cardinal Suite at Harpers Ferry Guest House
Harpers Ferry
10.0 out of 10, Exceptional, (22 reviews)
"Lovely room, easy check in/out, and thoughtful amenities. Would absolutely stay again!"
United States
Elizabeth
The price is CA $184
CA $278 total
includes taxes & fees
Mar 3 - Mar 4
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Find out more about Winchester

Winchester Guest Houses information

Number of reviews
350
Accommodation
19 Guest Houses
Lowest Price
CA $260
Highest Price
CA $554

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 $260 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.

Explore a world of travel with Expedia