Find a Bed and Breakfast in Winchester from CA $191

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

Browse Select Winchester B&B

Loudoun Valley Manor
Reception

Loudoun Valley Manor

3.0 star property
9.6 out of 10, Exceptional, (258)
"Very quiet and friendly staff"
The price is CA $191
CA $218 total
includes taxes & fees
Aug 27 - Aug 28
Loudoun Valley Manor
Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (90)
"The location is good."
The price is CA $372
CA $407 total
includes taxes & fees
Sep 10 - Sep 11
Glen Gordon Manor
Inn at Evergreen
Free daily full breakfast

Inn at Evergreen

3.5 star property
9.4 out of 10, Exceptional, (127)
"Wonderful place to stay"
The price is CA $275
CA $314 total
includes taxes & fees
Sep 9 - Sep 10
Inn at Evergreen
The Inn at Grass Roots Hill
Property entrance

The Inn at Grass Roots Hill

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazng views. Large rooms. Manager was very accommodating. Look forward to our next stay."
The price is CA $619
CA $706 total
includes taxes & fees
Sep 1 - Sep 2
The Inn at Grass Roots Hill
Hopkins Ordinary Bed Breakfast and Ale Works
Family House, Multiple Beds, Balcony, Garden Area | Balcony

Hopkins Ordinary Bed Breakfast and Ale Works

3.0 star property
10.0 out of 10, Exceptional, (31)
"Great place. Good food, great beer."
The price is CA $374
CA $409 total
includes taxes & fees
Sep 2 - Sep 3
Hopkins Ordinary Bed Breakfast and Ale Works
Stone Manor Boutique Inn
Garden

Stone Manor Boutique Inn

3.5 star property
9.6 out of 10, Exceptional, (93)
"It is a quiet and elegant property inside The breakfast was delicious and the owners were friendly and hospitable."
The price is CA $301
CA $343 total
includes taxes & fees
Aug 27 - Aug 28
Stone Manor Boutique Inn
Hillbrook Inn
Property amenity

Hillbrook Inn

4.0 star property
8.6 out of 10, Excellent, (668)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
The price is CA $267
CA $334 total
includes taxes & fees
Aug 28 - Aug 29
Hillbrook Inn
Gay Street Inn
Interior detail

Gay Street Inn

3.5 star property
10.0 out of 10, Exceptional, (33)
"Great place to stay in Washington VA to walk to inn at little Washington, patty O's (6 min walk), bakery, chocolates and rural landscape! "
The price is CA $496
CA $535 total
includes taxes & fees
Sep 3 - Sep 4
Gay Street Inn
The Carriage Inn B&B
Courtyard

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (425)
"Excellent, historic, amazing breakfast and hostess"
The price is CA $193
CA $219 total
includes taxes & fees
Sep 1 - Sep 2
The Carriage Inn B&B
Cantuta Inn
Garden

Cantuta Inn

3.0 star property
9.0 out of 10, Wonderful, (71)
"Clean and well taken care of. Owner was friendly and cooked a nice breakfast. A quick walk to the downtown of Harper's Ferry."
The price is CA $221
CA $248 total
includes taxes & fees
Sep 7 - Sep 8
Cantuta Inn
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Outdoor pool

Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view

9.8 out of 10, Exceptional, (34)
"It is an amazing place with a gorgeous view of the mountains and welcoming host"
The price is CA $449
CA $630 total
includes taxes & fees
Aug 29 - Aug 30
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Dining

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

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."
The price is CA $301
CA $431 total
includes taxes & fees
Sep 3 - Sep 4
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
The Van Gogh Room in Villa
Pool

The Van Gogh Room in Villa

9.0 out of 10, Wonderful, (63)
"Good stay. Beautiful view. Having never been to Purceville, I was taken aback by the fact that the establishment on s dirt road. "
The price is CA $415
CA $541 total
includes taxes & fees
Aug 28 - Aug 29
The Van Gogh Room in Villa
Timeless Elegance in Restored Suite – King Bed & Private Spa Bath
1 bedroom, WiFi, bed sheets

Timeless Elegance in Restored Suite – King Bed & Private Spa Bath

10.0 out of 10, Exceptional, (1)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved Stone Gables! Our room (The Leesburg) was lovely, and we had gorgeous weather to relax in the pool. It was quite expensive, but it was definitely worth it to us."
The price is CA $452
CA $890 total
includes taxes & fees
Aug 27 - Aug 28
Timeless Elegance in Restored Suite – King Bed & Private Spa Bath
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Exterior

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

2.0 star property
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."
The price is CA $2,441
CA $3,259 total
includes taxes & fees
Aug 27 - Aug 28
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
50's Drive-In Inside the Grand Castalian Inn B&B
Dining

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

2.0 star property
The price is CA $316
CA $452 total
includes taxes & fees
Sep 2 - Sep 3
50's Drive-In Inside the Grand Castalian Inn B&B
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Dining

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

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!"
The price is CA $316
CA $440 total
includes taxes & fees
Sep 14 - Sep 15
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Rustic Charm Meets Modern Comfort in Barn Loft Escape
Exterior

Rustic Charm Meets Modern Comfort in Barn Loft Escape

The price is CA $428
CA $858 total
includes taxes & fees
Aug 27 - Aug 28
Rustic Charm Meets Modern Comfort in Barn Loft Escape
Luxury King Suite w/ Private Entrance & Slate Walk-In Shower
1 bedroom, WiFi, bed sheets

Luxury King Suite w/ Private Entrance & Slate Walk-In Shower

The price is CA $413
CA $839 total
includes taxes & fees
Aug 27 - Aug 28
Luxury King Suite w/ Private Entrance & Slate Walk-In Shower
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Dining

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

10.0 out of 10, Exceptional, (2)
"We loved the spot and will be back!"
The price is CA $301
CA $433 total
includes taxes & fees
Sep 2 - Sep 3
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
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Motel 6 Winchester, VA

Motel 6 Winchester, VA

10/10 Excellent
"Stayed here several times over the course of a month. Rooms ways spotless, nice fridge and microwave. Treat your pets like family. Good motel, better than others of the same price. Only complaint was the doggie poop bags were out for over 24 hours, making clean up a chore."
Joy 2-night trip
Posted 13 hours ago
Motel 6 Winchester, VA

Find out more about Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
1,168
Accommodation
40 B&B
Lowest Price
CA $191
Highest Price
CA $619

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 $191 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.