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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Winchester bed & breakfast

Exterior
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (95)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is HK$2,092
HK$2,286 total
includes taxes & fees
20 Jan - 21 Jan 2026
Glen Gordon Manor
Reception
Loudoun Valley Manor

Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (276)
"Great location for visiting wineries"
United States
Anne
The price is HK$1,073
HK$1,224 total
includes taxes & fees
28 Dec - 29 Dec
Loudoun Valley Manor
Garden
Cantuta Inn

Cantuta Inn

Cantuta Inn
3.0 star property
Harpers Ferry
9.0 out of 10, Wonderful, (74)
"A comfortable, quiet, & beautiful place to stay. Staff was friendly and able to recommend somewhere good for dinner. "
United States
Aleta
The price is HK$1,205
HK$1,350 total
includes taxes & fees
29 Dec - 30 Dec
Cantuta Inn
Garden
Stone Manor Boutique Inn

Stone Manor Boutique Inn

Stone Manor Boutique Inn
3.5 star property
Lovettsville
9.6 out of 10, Exceptional, (95)
"The experience was very good, will return in the future. The breakfast was excellent. "
United States
Marvin
The price is HK$1,489
HK$1,697 total
includes taxes & fees
28 Dec - 29 Dec
Stone Manor Boutique Inn
Property amenity
Hillbrook Inn

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (671)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
The price is HK$1,187
HK$1,524 total
includes taxes & fees
14 Jan - 15 Jan 2026
Hillbrook Inn
Balcony
Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
Sperryville
10.0 out of 10, Exceptional, (31)
"Great place. Good food, great beer."
United States
Phil
Hopkins Ordinary Bed Breakfast and Ale Works
Free daily full breakfast
Inn at Evergreen

Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (132)
"Very nice cozy place and the breakfast was included and very delicious. Only issue I had was the footsteps of upstairs guests came through."
United States
Chiharu
Inn at Evergreen
Front of property
Inn of the Shenandoah

Inn of the Shenandoah

Inn of the Shenandoah
4.0 star property
Luray
9.8 out of 10, Exceptional, (40)
"It was an awesome place to stay!!"
United States
Eileen
The price is HK$2,352
HK$2,830 total
includes taxes & fees
7 Jan - 8 Jan 2026
Inn of the Shenandoah
Property entrance
The Inn at Grass Roots Hill

The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.2 out of 10, Wonderful, (7)
"House and property are absolutely beautiful. Staff are amazing and super friendly "
United States
Chad
The price is HK$3,568
HK$4,067 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Inn at Grass Roots Hill
Dining
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B

River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B

River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (3)
"My partner and I have both stayed in some pretty high end hotels and we were so impressed!! By far the best VRBO i’ve stayed in-newly renovated and decorated. You don’t want to pass up this hidden gem convenient to everything in Berkeley Springs!"
United States
Deirdre A.
The price is HK$1,511
HK$2,199 total
includes taxes & fees
19 Jan - 20 Jan 2026
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Interior detail
Gay Street Inn

Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (34)
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
The price is HK$2,792
HK$3,009 total
includes taxes & fees
1 Jan - 2 Jan 2026
Gay Street Inn
Outdoor pool
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Purcellville
9.8 out of 10, Exceptional, (36)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is HK$2,722
HK$3,732 total
includes taxes & fees
28 Dec - 29 Dec
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Pool
The Van Gogh Room in Villa

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (67)
"Wonderful "
United States
Joseph S.
The price is HK$2,333
HK$3,023 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Van Gogh Room in Villa
Dining
Appalachian Suite In Town!- The Grand Castalian Inn B&B

Appalachian Suite In Town!- The Grand Castalian Inn B&B

Appalachian Suite In Town!- The Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (2)
"We loved the spot and will be back!"
United States
Seth W.
The price is HK$1,511
HK$2,199 total
includes taxes & fees
19 Jan - 20 Jan 2026
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Courtyard
The Carriage Inn B&B

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (439)
"Excellent accommodations and breakfast. "
United States
William
The price is HK$1,245
HK$1,407 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Carriage Inn B&B
Dining
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B

Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B

Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (3)
"Beautiful house. Renovations are not quite complete yet, and the electronic locks needed extra communication with the owner to use, but still a great stay. Perfect location and this place will be gorgeous after renovations are complete."
United States
Daniel F.
The price is HK$1,422
HK$2,090 total
includes taxes & fees
19 Jan - 20 Jan 2026
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Dining
50's Drive-In Inside the Grand Castalian Inn B&B

50's Drive-In Inside the Grand Castalian Inn B&B

50's Drive-In Inside the Grand Castalian Inn B&B
2.0 star property
Berkeley Springs
The price is HK$1,601
HK$2,317 total
includes taxes & fees
19 Jan - 20 Jan 2026
50's Drive-In Inside the Grand Castalian Inn B&B
Exterior
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
2.0 star property
Lovettsville
10.0 out of 10, Exceptional, (1)
"Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend."
United States
Lukas D.
The price is HK$89,422
HK$117,023 total
includes taxes & fees
11 Jan - 12 Jan 2026
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
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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Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"I got in late and end up missing out on breakfast the next morning, but I was able to enjoy a good night's sleep in my spacious room and comfortable king size bed."
Douglas 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
1,142
Accommodation
34 B&B
Lowest Price
HK$1,224
Highest Price
HK$117,023

Frequently asked questions

Searching for B&Bs in Winchester?
Whether you're on a romantic holiday and want to stay somewhere quiet, or you're travelling solo and looking to chat with locals, B&Bs can be a great choice for many travellers. If your ideal holiday to Winchester includes spending lots of time outside, Jim Barnett Park and Star Fort Civil War Battlefield are good spots to enjoy the scenery.
Why consider a B&B over a traditional hotel room?
Every B&B has a unique charm — whether it's a cosy reading space or a sunlit breakfast nook, the quaint details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Winchester?
Here are some B&Bs in the area: Hillbrook Inn: 9 rooms. 13.5 mi (21.7 km) from the heart of Winchester. Enjoy the free full breakfast and fitness centre. The Carriage Inn B&B: 7 rooms. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the designer toiletries and in-room fireplace.
What's the best time of year to stay at a B&B in Winchester?
When you're planning your getaway to Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
What is there to do in Winchester?
Travellers who want to experience Winchester should visit its interesting historical sites and major shopping area. When you want to spend some time in the great outdoors, Jim Barnett Park and Star Fort Civil War Battlefield are some notable spots. You should put Bright Box Theater and Shenandoah Valley Discovery Museum on your list if you want to see more of the area.
How can I get to and around Winchester?
Planning your excursions in and around Winchester is easier with these transportation options. Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the heart of the city. Otherwise, you can search for flights to Washington Dulles International Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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