Search Guest Houses in Winchester

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 35 Guest Houses in Winchester with updated reviews, rates, and availability.

White Moose Inn
Exterior

White Moose Inn

4.0 star property
9.8 out of 10, Exceptional, (135)
"Perfect location and stay to combine with dinner at the Inn at Little Washington."
The price is SAR 1,309
SAR 1,411 total
includes taxes & fees
7 May - 8 May
White Moose Inn
The Bluebird Suite at Harpers Ferry Guest House
1 bedroom, free WiFi, bed sheets

The Bluebird Suite at Harpers Ferry Guest House

10.0 out of 10, Exceptional, (46)
"The location was great! It was within walking distance of Harpers Ferry and many establishments. The room was beautiful and the added touch of coffee and breakfast items made us feel at home. We would definitely recommend staying here!"
The price is SAR 589
SAR 857 total
includes taxes & fees
30 Apr - 1 May
The Bluebird Suite at Harpers Ferry Guest House
Sojourn at The Legacy Inn- The Cash & Carter Suite
Terrace/patio

Sojourn at The Legacy Inn- The Cash & Carter Suite

10.0 out of 10, Exceptional, (3)
"We loved our room and the property So close we could walk to town. It was great having the walking / biking trail right behind the property. We had a great stay."
Sojourn at The Legacy Inn- The Cash & Carter Suite
►New! Unique Custom Crafted Train Station Lodge W/ private walking trails
2 bedrooms, desk, iron/ironing board, free WiFi

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

10.0 out of 10, Exceptional, (13)
"Very unique, quiet, and cozy. "
The price is SAR 450
SAR 1,132 total
includes taxes & fees
30 Apr - 1 May
►New! Unique Custom Crafted Train Station Lodge W/ private walking trails
The Cardinal Suite at Harpers Ferry Guest House
Exterior

The Cardinal Suite at Harpers Ferry Guest House

10.0 out of 10, Exceptional, (17)
"The Guest House in Harpers Ferry was the perfect place to enjoy a fun weekend away. The room is just as advertised and Cathy and Bryan have thought of everything to make your stay enjoyable!"
The price is SAR 671
SAR 973 total
includes taxes & fees
29 May - 30 May
The Cardinal Suite at Harpers Ferry Guest House
The Goldfinch Suite at Harpers Ferry Guest House
Exterior

The Goldfinch Suite at Harpers Ferry Guest House

10.0 out of 10, Exceptional, (37)
"Great location! Close to walk to restaurants, activities"
The price is SAR 589
SAR 865 total
includes taxes & fees
30 Apr - 1 May
The Goldfinch Suite at Harpers Ferry Guest House
Briar Patch Bed & Breakfast Inn
Seasonal outdoor pool

Briar Patch Bed & Breakfast Inn

3.0 star property
7.8 out of 10, Good, (8)
"The room was so charming and cozy. really nice linens and very comfortable bed. The Inn Keeper, Dan, was fun and knew a lot about the area. Dan is also a great breakfast chef! "
The price is SAR 1,341
SAR 1,529 total
includes taxes & fees
30 Apr - 1 May
Briar Patch Bed & Breakfast Inn
The Chickadee Room at Harpers Ferry Guest House
Exterior

The Chickadee Room at Harpers Ferry Guest House

9.8 out of 10, Exceptional, (9)
"We enjoyed our stay. We liked the room and the fact it was close to town which made going places easy. "
The price is SAR 461
SAR 702 total
includes taxes & fees
29 May - 30 May
The Chickadee Room at Harpers Ferry Guest House
Sojourn at The Legacy Inn-The Bonnie & Clyde Suite
Property grounds

Sojourn at The Legacy Inn-The Bonnie & Clyde Suite

8.0 out of 10, Very Good, (1)
"Beautiful little gem. PM had good communication,there was a little issue with the front door code when we got there, but I messaged them and they promptly responded with a correct code. Only real issue was the place was a little "dirty". Looked like whoever cleaned did not dust, or sweep (dead crickets, broken glass near toilet in bathroom), or wipe down the nite stand (rings from past cups). With a 45 cleaning fee, I'd expect the place to be a little more clean. For me personally I would prefer...
Sojourn at The Legacy Inn-The Bonnie & Clyde Suite
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed
Property grounds

Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed

2.0 star property
10.0 out of 10, Exceptional, (11)
"Going to visit Luray caverns and the Shenandoah mountains while out at this beautiful tiny home was amazing for the weekend."
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed
Secret Gardens Carriage House
Property grounds

Secret Gardens Carriage House

2.0 star property
9.8 out of 10, Exceptional, (19)
"Winchester was such a lovely town with so many things to do and see. We enjoyed coming home to the cottage each night with its screened-in patio and relaxing view of flowers and shade trees. The cottage was cozy and clean with plenty of linens and staples. I would stay here again, the location was excellent."
Secret Gardens Carriage House
Shenandoah Mountain House - Guest Suite
Fridge, microwave, stovetop, dishwasher

Shenandoah Mountain House - Guest Suite

10.0 out of 10, Exceptional, (5)
"Very stylish, organized and located by so many attractions. Highly recommend for a small group. "
The price is SAR 431
SAR 1,010 total
includes taxes & fees
1 May - 2 May
Shenandoah Mountain House - Guest Suite
Guest House at Mt. Independence
Full-size fridge, microwave, oven, stovetop

Guest House at Mt. Independence

4.0 star property
10.0 out of 10, Exceptional, (3)
"Beautiful Guest House well appointed on beautiful acreage. Would encourage everyone to visit. Host was very helpful and accommodating. You will enjoy the stay ! "
Guest House at Mt. Independence
Riverview Suite at La Soledad
TV, fireplace

Riverview Suite at La Soledad

10.0 out of 10, Exceptional, (3)
"River Views Lavender Farm was an exceptional place to stay! Upon arrival we were greeted by 3 very happy and friendly dogs! The room was very comfortable and met all our needs. We opened up the windows and enjoyed listening to the sound of the river below and admiring the beauty all around. There was an issue with the internet connection not working, we were in communication with our host often and the issue was resolved in a timely manner. We enjoyed delicious meals at Cannonball Deli and...
The price is SAR 923
SAR 1,350 total
includes taxes & fees
30 Apr - 1 May
Riverview Suite at La Soledad
Sojourn at The Legacy Inn- The Kennedy Suite
Terrace/patio

Sojourn at The Legacy Inn- The Kennedy Suite

10.0 out of 10, Exceptional, (1)
"The room was what was stated in the app. Clean, easy access "
Sojourn at The Legacy Inn- The Kennedy Suite
Sojourn at The Legacy Inn- The Parton Suite
Terrace/patio

Sojourn at The Legacy Inn- The Parton Suite

Sojourn at The Legacy Inn- The Parton Suite
Sojourn at The Legacy Inn- The King Suite
Terrace/patio

Sojourn at The Legacy Inn- The King Suite

8.0 out of 10, Very Good, (1)
Sojourn at The Legacy Inn- The King Suite
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
Exterior

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

10.0 out of 10, Exceptional, (3)
"This was a great place to escape to! Very quiet and peaceful but close to some great restaurants and vineyards."
The price is SAR 1,032
SAR 1,606 total
includes taxes & fees
1 May - 2 May
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
Guest House at Mt Independence
2 bedrooms, desk, iron/ironing board, free WiFi

Guest House at Mt Independence

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property, conveniently located to attractions. Host was extremely responsive and friendly. Home and surrounding property was immaculate. We will be staying here again when back in the area. "
The price is SAR 638
SAR 1,101 total
includes taxes & fees
30 Apr - 1 May
Guest House at Mt Independence
Sojourn at The Legacy Inn- The Eden Suite
Terrace/patio

Sojourn at The Legacy Inn- The Eden Suite

10.0 out of 10, Exceptional, (3)
"We loved the two room suite. It was perfect for visiting with daughter and playing games. We will definitely be back."
Sojourn at The Legacy Inn- The Eden Suite
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Dreamtime - Modern A-frame Cabin w/ Hot tub
Smart TV, fireplace, books

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"Great cabin. Clean and so welcoming"
The price is SAR 1,084
SAR 1,373 total
includes taxes & fees
7 May - 8 May
Dreamtime - Modern A-frame Cabin w/ Hot tub
Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (312)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Terrace/patio

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (97)
"This was a perfect clean comfortable place to stay while exploring the Harper's Ferry area. Hosts Scott and Margie are friendly and welcoming"
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
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.