Search Guest Houses in Winchester

Compare 27 Guest Houses in Winchester with updated reviews, rates, and availability.

White Moose Inn

4.0 star property
9.8 out of 10, Exceptional, (125)
"Excellent service and location. Loved the breakfast. "
The price is AED 1,212
AED 1,307 total
includes taxes & fees
15 Jan - 16 January 2025
White Moose Inn

Briar Patch Bed & Breakfast Inn

3.0 star property
7.6 out of 10, Good, (7)
"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 1,010
AED 1,151 total
includes taxes & fees
24 Dec - 25 Dec
Briar Patch Bed & Breakfast Inn

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!!!"
The price is AED 283
AED 565 total
includes taxes & fees
24 Dec - 25 Dec
Sojourn at The Legacy Inn- The Cash & Carter Suite

The Bluebird Suite at Harpers Ferry Guest House

10.0 out of 10, Exceptional, (44)
"Quaint, amazing location, loved the in-room breakfast and snacks. Easy to check in and out, and quick response from owners for all questions."
The price is AED 514
AED 649 total
includes taxes & fees
29 Dec - 30 Dec
The Bluebird 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 Goldfinch Suite at Harpers Ferry Guest House

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

10.0 out of 10, Exceptional, (11)
"From the moment we walked into this incredible home, we were completely captivated by its uniqueness. The toy train set that loops around the ceiling above the dining room was a delightful surprise—our family was in awe of it, and the kids couldn’t get enough of watching it go around! The custom bunk beds were another huge hit with the little ones, adding an extra touch of charm and fun. As for my wife and I, we truly appreciated the privacy and comfort of the master bedroom on the second...
►New! Unique Custom Crafted Train Station Lodge W/ private walking trails

Riverview Suite at La Soledad

10.0 out of 10, Exceptional, (2)
"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...
Riverview Suite at La Soledad

Guest House at Mt. Independence

4.0 star property
Guest House at Mt. Independence

Guest House at 1796 Historic Farm in Wine Country

10.0 out of 10, Exceptional, (71)
"I love this property. I came for a return visit, so I knew what to expect. We enjoyed wine by the firepit each night. Thank you! The accommodations are quaint yet top notch. The host family is generous, communicative and accommodating and also respectful of the privacy that we wanted. I book well in advance to make sure I get the date I want to see the Fall colors--there is nowhere better to do this! Thank you!! "
Guest House at 1796 Historic Farm in Wine Country

Shenandoah Valley mountain views in cozy guest suite

10.0 out of 10, Exceptional, (4)
"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. "
Shenandoah Valley mountain views in cozy guest suite

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 Chickadee Room at Harpers Ferry Guest House

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 1,612 total
includes taxes & fees
24 Dec - 25 Dec
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

Sojourn at The Legacy Inn- The King Suite

8.0 out of 10, Very Good, (1)
The price is AED 283
AED 565 total
includes taxes & fees
24 Dec - 25 Dec
Sojourn at The Legacy Inn- The King Suite

The Cardinal Suite at Harpers Ferry Guest House

10.0 out of 10, Exceptional, (15)
"We had questions and the owner responded right away and took good care of us. Would definitely recommend this place and would stay there again if the opportunity arises."
The Cardinal Suite at Harpers Ferry Guest House

Sojourn at The Legacy Inn- The Parton Suite

The price is AED 441
AED 783 total
includes taxes & fees
24 Dec - 25 Dec
Sojourn at The Legacy Inn- The Parton Suite

Sojourn at The Legacy Inn- The Eden Suite

The price is AED 525
AED 973 total
includes taxes & fees
24 Dec - 25 Dec
Sojourn at The Legacy Inn- The Eden Suite

Sojourn at The Legacy Inn- The Adam's Suite

9.0 out of 10, Wonderful, (2)
"What an absolutely adorable Inn. Everything was excellent. We really enjoyed our stay here. Very quiet. Very cleaned. Overall 5+ stars. We will definitely come back again."
The price is AED 283
AED 565 total
includes taxes & fees
5 Jan - 6 January 2025
Sojourn at The Legacy Inn- The Adam's Suite

The Legacy Inn Luray Virginia

3.0 star property
8.0 out of 10, Very Good, (25)
"The Legacy Inn felt like home. If you're looking for a quiet getaway that's in the heart of downtown Luray then I would highly recommend them. This has been my second visit and I will be a staying again in the very near future! "
The Legacy Inn Luray Virginia

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 "
Guest House at Mt. Independence

Sojourn at The Legacy Inn - All 7 Suites

The price is AED 5,050
AED 7,505 total
includes taxes & fees
25 Dec - 26 Dec
Sojourn at The Legacy Inn - All 7 Suites
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

Hidden Gem in the woods with hot tub

9.6 out of 10, Exceptional, (66)
"Nice"
Hidden Gem in the woods with hot tub

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (162)
"It's the perfect cozy place for two for Thanksgiving. The indoor fireplace has plenty of firewood, and the outdoor firepit has a grill plate, perfect for making smores. We started our mornings having coffee in the hot tub. We will stay here again! "
Secluded, Cozy Cottage in the Shenandoah Valley

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
The price is AED 1,021
AED 2,383 total
includes taxes & fees
26 Dec - 27 Dec
Terra Alta - Incredible River Views and Hot Tub!
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.