Search B&B in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
3 Apr - 5 Apr
In two weeks
10 Apr - 12 Apr
In one month
24 Apr - 26 Apr
In two months
22 May - 24 May

Our top choices for Winchester bed & breakfast

Exterior

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (96 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
The price is HK$2,342
HK$2,560 total
includes taxes & fees
15 Apr - 16 Apr
Glen Gordon Manor
Garden view

Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (284 reviews)
"Olga is great and the beds were super comfy. "
United States
Tyler
The price is HK$1,081
HK$1,233 total
includes taxes & fees
30 Mar - 31 Mar
Loudoun Valley Manor
Hallway

Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (133 reviews)
"Beautiful property and excellent food."
United States
Paula
The price is HK$1,824
HK$2,079 total
includes taxes & fees
30 Mar - 31 Mar
Inn at Evergreen
Front of property

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (676 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is HK$1,196
HK$1,536 total
includes taxes & fees
31 Mar - 1 Apr
Hillbrook Inn
Front of property

Stone Manor Boutique Inn

Stone Manor Boutique Inn
3.5 star property
Lovettsville
9.6 out of 10, Exceptional, (98 reviews)
"The breakfast was fabulous and the room great "
United States
MICHEL
The price is HK$1,621
HK$1,848 total
includes taxes & fees
30 Mar - 31 Mar
Stone Manor Boutique Inn
Interior

Light Horse Inn: Suite 4

Light Horse Inn: Suite 4
Harpers Ferry
10.0 out of 10, Exceptional, (13 reviews)
"Very charming and comfortable "
United States
Joseph
The price is HK$1,449
HK$1,848 total
includes taxes & fees
1 Apr - 2 Apr
Light Horse Inn: Suite 4
Exterior

Cantuta Inn

Cantuta Inn
3.0 star property
Harpers Ferry
9.0 out of 10, Wonderful, (76 reviews)
"The hostess and her husband were friendly and made us feel very welcome! Breakfast was scrambled eggs with fruit and was nice."
United States
Ron
The price is HK$1,292
HK$1,447 total
includes taxes & fees
30 Mar - 31 Mar
Cantuta Inn
Interior

Light Horse Inn: Suite 6

Light Horse Inn: Suite 6
Bolivar
9.8 out of 10, Exceptional, (6 reviews)
"Great spot!"
United States
Theresa
The price is HK$1,371
HK$1,735 total
includes taxes & fees
30 Mar - 31 Mar
Light Horse Inn: Suite 6
Outdoor dining

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (67 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
The price is HK$2,350
HK$3,036 total
includes taxes & fees
30 Mar - 31 Mar
The Van Gogh Room in Villa
Garden

Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
Sperryville
9.8 out of 10, Exceptional, (33 reviews)
"Great place. Good food, great beer."
United States
Phil
The price is HK$1,965
HK$2,148 total
includes taxes & fees
30 Mar - 31 Mar
Hopkins Ordinary Bed Breakfast and Ale Works
Interior entrance

The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.4 out of 10, Exceptional, (8 reviews)
"Beautiful venue, great service, and very close to the local downtown. Would stay again, highly recommend. "
United States
Robert
The price is HK$3,594
HK$4,097 total
includes taxes & fees
30 Mar - 31 Mar
The Inn at Grass Roots Hill
Porch

Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
The price is HK$2,812
HK$3,031 total
includes taxes & fees
14 Apr - 15 Apr
Gay Street Inn
Outdoor dining

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, (37 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is HK$2,741
HK$3,714 total
includes taxes & fees
30 Mar - 31 Mar
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Front of property

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (443 reviews)
"Lovely inn with gracious hosts and fabulous breakfast. "
United States
Megan
The price is HK$1,148
HK$1,298 total
includes taxes & fees
14 Apr - 15 Apr
The Carriage Inn B&B
Exterior

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 reviews)
"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$1,612
HK$2,283 total
includes taxes & fees
9 Apr - 10 Apr
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Interior

Light Horse Inn: Suite 2

Light Horse Inn: Suite 2
Harpers Ferry
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay. Staff exceptionally friendly"
United States
Michael
The price is HK$1,292
HK$1,675 total
includes taxes & fees
6 Apr - 7 Apr
Light Horse Inn: Suite 2
Interior

Light Horse Inn: Suite 7

Light Horse Inn: Suite 7
Bolivar
9.2 out of 10, Wonderful, (5 reviews)
"The property was well-kept, and breakfast was delicious with friendly staff and guests."
United States
Rebecca
The price is HK$1,371
HK$1,735 total
includes taxes & fees
30 Mar - 31 Mar
Light Horse Inn: Suite 7
Exterior

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 reviews)
"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$1,702
HK$2,393 total
includes taxes & fees
9 Apr - 10 Apr
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Exterior

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 reviews)
"We loved the spot and will be back!"
United States
Seth W.
The price is HK$1,702
HK$2,393 total
includes taxes & fees
9 Apr - 10 Apr
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Exterior

Light Horse Inn: Suite 3

Light Horse Inn: Suite 3
Harpers Ferry
The price is HK$1,449
HK$1,858 total
includes taxes & fees
7 Apr - 8 Apr
Light Horse Inn: Suite 3
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Love this property. Will stay again! Beautiful rooms"
Heather 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
1,959
Accommodation
34 B&B
Lowest Price
HK$1,233
Highest Price
HK$4,097

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?
Below are some well-liked B&Bs in the surrounding area: The Carriage Inn B&B: 7 rooms. 18.2 mi (29.3 km) from the city centre. Enjoy the designer toiletries and in-room fireplace. Hillbrook Inn: 9 rooms. Situated 13.5 mi (21.7 km) from the heart of Winchester. Enjoy the free full breakfast and fitness centre.
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.

Explore a world of travel with Expedia