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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, (135)
"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
7 May - 8 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 827 total
includes taxes & fees
2 Jun - 3 Jun
The Bluebird Suite at Harpers Ferry Guest House

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

10.0 out of 10, Exceptional, (13)
"Very unique, quiet, and cozy. "
The price is AED 441
AED 1,100 total
includes taxes & fees
6 May - 7 May
►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
28 May - 29 May
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 847 total
includes taxes & fees
13 May - 14 May
The Goldfinch Suite at Harpers Ferry Guest House

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 AED 1,313
AED 1,497 total
includes taxes & fees
5 May - 6 May
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 687 total
includes taxes & fees
8 May - 9 May
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)
"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

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

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 AED 1,017
AED 1,689 total
includes taxes & fees
24 May - 25 May
Shenandoah Mountain House - Guest Suite

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

10.0 out of 10, Exceptional, (4)
"We came to get away from the city for a few days. This was the perfect location to relax with river views but close enough to walk to downtown for food. The Host was very friendly and we loved the room. "
The price is AED 970
AED 1,408 total
includes taxes & fees
6 May - 7 May
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)
"This was a great place to escape to! Very quiet and peaceful but close to some great restaurants and vineyards."
The price is AED 1,010
AED 1,573 total
includes taxes & fees
6 May - 7 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)
"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 AED 624
AED 1,082 total
includes taxes & fees
5 May - 6 May
Guest House at Mt Independence

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.
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Other property types in Winchester

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (313)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"Great cabin. Clean and so welcoming"
The price is AED 1,062
AED 1,329 total
includes taxes & fees
28 May - 29 May
Dreamtime - Modern A-frame Cabin w/ Hot tub

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

9.2 out of 10, Wonderful, (13)
"Week with elderly family members and this home was a good spot to rest and relax. Upon arrival, house was neat and clean. Well stocked with cooking items. Nice layout. Good central locations for day trip options. Overall I would recommend this home. "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
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.