Find a Bed and Breakfast in Winchester from CA $214

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Winchester bed & breakfast

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 CA $406
CA $444 total
includes taxes & fees
May 5 - May 6
Glen Gordon Manor

Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (292 reviews)
"Amazing inn, clean, owner is friendly."
United States
Miguel
The price is CA $187
CA $214 total
includes taxes & fees
May 4 - May 5
Loudoun Valley Manor

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (677 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is CA $203
CA $261 total
includes taxes & fees
May 12 - May 13
Hillbrook Inn

Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (135 reviews)
"Beautiful historic inn! Gorgeous property and close to everything! Can’t wait to visit again."
United States
Kristine
The price is CA $340
CA $387 total
includes taxes & fees
Jun 1 - Jun 2
Inn at Evergreen

Stone Manor Boutique Inn

Stone Manor Boutique Inn
3.5 star property
Lovettsville
9.6 out of 10, Exceptional, (101 reviews)
"This is a beautiful place to stay. Immaculate. Room was very clean and nice. Staff is very friendly. Dining area is very nice. I highly recommend staying at this inn!"
United States
Meera
The price is CA $281
CA $320 total
includes taxes & fees
May 4 - May 5
Stone Manor Boutique Inn

Light Horse Inn: Suite 7

Light Horse Inn: Suite 7
Bolivar
9.4 out of 10, Exceptional, (6 reviews)
"The property was well-kept, and breakfast was delicious with friendly staff and guests."
United States
Rebecca
The price is CA $238
CA $302 total
includes taxes & fees
May 3 - May 4
Light Horse Inn: Suite 7

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (68 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
The price is CA $407
CA $530 total
includes taxes & fees
May 3 - May 4
The Van Gogh Room in Villa

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 CA $251
CA $320 total
includes taxes & fees
May 7 - May 8
Light Horse Inn: Suite 4

The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.2 out of 10, Wonderful, (10 reviews)
"Beautiful venue, great service, and very close to the local downtown. Would stay again, highly recommend. "
United States
Robert
The price is CA $561
CA $639 total
includes taxes & fees
May 15 - May 16
The Inn at Grass Roots Hill

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, (34 reviews)
"Great place. Good food, great beer."
United States
Phil
The price is CA $355
CA $389 total
includes taxes & fees
May 4 - May 5
Hopkins Ordinary Bed Breakfast and Ale Works

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)
"My husband and I had a memorable stay at Villa Maud over New Year. Maud was a gracious host and we very much enjoyed the comforts of our honeymoon villa. Maud is a talented artist and her impressive work adorns the villa. One of the highlights was meeting Tim the donkey"
United States
jo H.
The price is CA $475
CA $664 total
includes taxes & fees
May 8 - May 9
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Cantuta Inn

Cantuta Inn
3.0 star property
Harpers Ferry
9.0 out of 10, Wonderful, (76 reviews)
"Clean, great location, courteous staff. Could not ask for better."
United States
Anthony
The price is CA $242
CA $271 total
includes taxes & fees
May 4 - May 5
Cantuta Inn

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (447 reviews)
"Lovely inn with gracious hosts and fabulous breakfast. "
United States
Megan
The price is CA $211
CA $238 total
includes taxes & fees
May 18 - May 19
The Carriage Inn B&B

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 CA $488
CA $526 total
includes taxes & fees
May 7 - May 8
Gay Street Inn

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 CA $224
CA $295 total
includes taxes & fees
May 6 - May 7
Light Horse Inn: Suite 2

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 CA $280
CA $405 total
includes taxes & fees
May 3 - May 4
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B

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 CA $238
CA $302 total
includes taxes & fees
May 3 - May 4
Light Horse Inn: Suite 6

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

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Lovettsville
10.0 out of 10, Exceptional, (1 review)
"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 CA $15,618
CA $20,066 total
includes taxes & fees
May 4 - May 5
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

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 CA $295
CA $424 total
includes taxes & fees
May 3 - May 4
River Retreat Suite In Town!- Inside 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 reviews)
"We loved the spot and will be back!"
United States
Seth W.
The price is CA $295
CA $424 total
includes taxes & fees
May 3 - May 4
Appalachian Suite In Town!- The Grand Castalian Inn B&B
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Find out more about Winchester

Winchester B&B information

Number of reviews
1,319
Accommodation
40 B&B
Lowest Price
CA $214
Highest Price
CA $20,066

Frequently asked questions

What is the nightly rate for a B&B in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from CA $214 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Winchester?
The best time to book a B&B in Winchester is during the vibrant spring months of March to May. This period sees the city come alive with blooming flowers and outdoor events, making it a splendid time for travellers looking to enjoy the rich history and scenic beauty of the area. With pleasant temperatures averaging in the mid-teens Celsius, exploring Winchester's historic sites, such as the iconic Winchester Cathedral and the Great Hall, becomes a delightful experience.

April, in particular, is a popular choice for visitors, as it offers a wonderful blend of comfortable weather and lively local festivals, such as the Winchester Science Festival. The mild climate encourages outdoor strolls through the picturesque gardens and along the River Itchen, superb for those who appreciate a blend of culture and nature.

For those seeking a more budget-friendly option, consider visiting in November. This month allows for a quieter experience, where you can enjoy the charm of Winchester's historic streets adorned for the festive season. It's an ideal time for leisurely exploration, with the city's attractions less crowded and often offering special events and markets.
What is the difference between a Winchester B&B and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

Explore a world of travel with Expedia