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

White Moose Inn

4.0 star property
9.8 out of 10, Exceptional, (134)
"Perfect location and stay to combine with dinner at the Inn at Little Washington."
The price is AED 1,282
AED 1,382 total
includes taxes & fees
1 May - 2 May
White Moose Inn

The Bluebird Suite at Harpers Ferry Guest House

10.0 out of 10, Exceptional, (46)
"This property is in an ideal location, very very clean, exactly as described Would definitely recommend and hopefully will book again our visit. "
The price is AED 577
AED 839 total
includes taxes & fees
28 Apr - 29 Apr
The Bluebird Suite at Harpers Ferry Guest House

Sojourn at The Legacy Inn- The Cash & Carter Suite

10.0 out of 10, Exceptional, (3)
"This is an exceptional property! My wife and I spent a night here and had access to the living room where we hing out and played games and our cash and carter room was super comfortable, clean and we will be back! We took advantage of the i e maker AND restaurants/ Main Street was a very short walk away on Lurays river walk. We did the entire walk with our dog and visited a few bakeries who were true artisans! LOVED OUR VISIT!!!"
Sojourn at The Legacy Inn- The Cash & Carter Suite

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

10.0 out of 10, Exceptional, (12)
"This is such a gem. House is perfectly set up for a family to have fun and comfy sleep. It’s beautiful. I love the train theme! Thank you ! "
The price is AED 441
AED 1,108 total
includes taxes & fees
29 Apr - 30 Apr
►New! Unique Custom Crafted Train Station Lodge W/ private walking trails

The Cardinal Suite at Harpers Ferry Guest House

10.0 out of 10, Exceptional, (17)
"Perfect for a little weekend getaway. Super clean, comfy bed, large than expected bathroom, easy parking, fridge and basket with breakfast options. Only downside was no ice. "
The price is AED 657
AED 953 total
includes taxes & fees
27 Apr - 28 Apr
The Cardinal Suite at Harpers Ferry Guest House

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 AED 577
AED 851 total
includes taxes & fees
27 Apr - 28 Apr
The Goldfinch Suite at Harpers Ferry Guest House

Briar Patch Bed & Breakfast Inn

3.0 star property
7.8 out of 10, Good, (8)
"Charming but rustic farm property with outbuildings. Eclectic, NOT fancy. Very clean, not manicured. This is like staying at a real farm. "
The price is AED 1,313
AED 1,497 total
includes taxes & fees
25 Apr - 26 Apr
Briar Patch Bed & Breakfast Inn

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 AED 452
AED 691 total
includes taxes & fees
28 Apr - 29 Apr
The Chickadee Room at Harpers Ferry Guest House

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

2.0 star property
10.0 out of 10, Exceptional, (11)
"Convenient location in Winchester though the property made it feel like you are in the country. Check in time must be precise as the owner needs to explain a couple things and let you in. This was good as my husband had a couple questions. Toaster oven was missing its tray so it was not easy to use the appliance. Coffee maker and refrigerator work great, bathroom facilities work. The house is in great condition and a neat place to stay."
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed

Secret Gardens Carriage House

2.0 star property
9.8 out of 10, Exceptional, (19)
"We are so glad we stumbled upon this gem! Looking to find a place to celebrate our anniversary & get away (long overdue), I found Ramana’s garden paradise. It is a quaint 1920’s carriage house with beautiful hardwood floors, a pedestal tub, fully stocked kitchen & large screened in porch for relaxing on those gorgeous evenings! Upon arrival, Ramana greeted us with our keys & a tour of the whole property, including where we would be staying, showing us where we could find organic veggies & herbs...
Secret Gardens Carriage House

Shenandoah Mountain House - Guest Suite

10.0 out of 10, Exceptional, (5)
"We had a lovely stay! If the weather had been better, I know we would have taken advantage of all the outdoor amenities -- big porch and fire pit. Ferhan was very responisve to any questions we had. "
The price is AED 422
AED 989 total
includes taxes & fees
27 Apr - 28 Apr
Shenandoah Mountain House - Guest Suite

Guest House at Mt. Independence

4.0 star property
10.0 out of 10, Exceptional, (3)
"This is the perfect couple's heaven. Beautifully decorated, art in every corner. Comfortable bed, relaxing tub and cozy living room couch. The property is gorgeous and very quiet. 10min away from nice restaurants, bakery and more than a dozen wineries. The national park is just 5min away with great trails and breath taking views. Stephen is very attentive and you can add many services to your stay. My husband and I had the most amazing time and can't wait to be back. "
Guest House at Mt. Independence

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 AED 904
AED 1,318 total
includes taxes & fees
27 Apr - 28 Apr
Riverview Suite at La Soledad

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

Sojourn at The Legacy Inn- The Parton Suite

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

10.0 out of 10, Exceptional, (3)
"Absolutely loved our stay at Unicorn Hollow. So peaceful. Clean and had everything you needed. Loved the horses and Guiseppe (the donkey) along with the deer and alpacas. Can stroll about the property. Anna and Pino were wonderful to meet. "
The price is AED 1,010
AED 1,573 total
includes taxes & fees
1 May - 2 May
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

Guest House at Mt Independence

2.0 star property
10.0 out of 10, Exceptional, (2)
"Had a great time arching the sun rise and set over the blue ridge mountains "
The price is AED 683
AED 1,132 total
includes taxes & fees
13 May - 14 May
Guest House at Mt Independence

Sojourn at The Legacy Inn- The Eden Suite

10.0 out of 10, Exceptional, (3)
"Very clean. My only gripe was that they should have a maintenance person to maintenance all the furnitures and upholstery. The living room table legs were loose and wobbling and the tower hangers in the bathrooms were almost coming off the wall. Little tidy maintenance will make it much better. "
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.
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Other property types in Winchester

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (312)
"This was absolutely just what we needed! The view was so breathtaking and the serenity of this place is to die for! I was very pleased with our stay here and we will definitely be returning de"
Star view cabin-Riverfront

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"Lovely cabin, very clean and well maintained. A girlfriend weekend and we wanted a great place to hang out and this fit the bill. We never got the TV to work but could be user error. "
The price is AED 1,062
AED 1,333 total
includes taxes & fees
30 Apr - 1 May
Dreamtime - Modern A-frame Cabin w/ Hot tub

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

9.8 out of 10, Exceptional, (96)
"1st time visiting the East Coast and our stay in this beautiful, quaint home was perfect! We felt the warm welcome as soon as we walked in and enjoyed the thoughtful complimentary items. The house was close to Harper’s Ferry & neighboring cities, lots to do in close proximity. Enjoyed the porch on our last night as we sat and listened to the rain and the sound of the river. Host was very attentive & prompt. Definitely recommend as a place to stay for a small family!"
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.