Search B&B in Winchester

    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
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Browse Select Winchester B&B

Our top choices for Winchester bed & breakfast

Loudoun Valley Manor
Reception

Loudoun Valley Manor

3.0 star property
9.6 out of 10, Exceptional, (257)
"The area is beautiful close to many wineries and brewers. Nice trip to Harper's Ferry and a great restaurant. Our room and bathroom was very nice and large Breakfast was great, eggs to order with pastries, fruits, muffins etc.."
The price is Rp2.436.900
Rp2.778.066 total
includes taxes & fees
7 Sept - 8 Sept
Loudoun Valley Manor
Lily Garden Bed and Breakfast
Front of property

Lily Garden Bed and Breakfast

2.5 star property
9.6 out of 10, Exceptional, (71)
"The facility is quite small, even for 2 adults. There were ants on the counters. The provided breakfast was wonderful and plentiful. Nicely decorated. "
Lily Garden Bed and Breakfast
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 Rp2.737.126
Rp3.092.953 total
includes taxes & fees
1 Sept - 2 Sept
The Carriage Inn B&B
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 Rp3.238.128
Rp4.033.504 total
includes taxes & fees
24 Aug - 25 Aug
Hillbrook Inn
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 Rp3.362.922
Rp3.833.731 total
includes taxes & fees
24 Aug - 25 Aug
Inn at Evergreen
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 Rp3.536.719
Rp4.031.876 total
includes taxes & fees
25 Aug - 26 Aug
Stone Manor Boutique Inn
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 Rp2.603.520
Rp2.915.942 total
includes taxes & fees
8 Sept - 9 Sept
Cantuta Inn
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 Rp4.051.728
Rp4.428.588 total
includes taxes & fees
25 Aug - 26 Aug
Glen Gordon Manor
Mayneview B&B
Outdoor spa tub

Mayneview B&B

4.0 star property
8.2 out of 10, Very good, (413)
"Fabulous place to stay, beautiful and clean, delicious breakfast, easy access to Shenandoah National Park, close to the little downtown area. "
Mayneview B&B
Maria's Garden and Inn
Porch

Maria's Garden and Inn

3.0 star property
9.4 out of 10, Exceptional, (125)
"Wonderful stay wonderful hosts great breakfast!"
Maria's Garden and Inn
Inn of the Shenandoah
Front of property

Inn of the Shenandoah

4.0 star property
9.8 out of 10, Exceptional, (40)
"It was an awesome place to stay!!"
Inn of the Shenandoah
The Manor at Courtland Farm
Outdoor pool

The Manor at Courtland Farm

3.5 star property
9.2 out of 10, Wonderful, (47)
"This was one of the most beautiful places I have ever stayed. The service was excellent!"
The Manor at Courtland Farm
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 Rp7.466.407
Rp8.511.707 total
includes taxes & fees
22 Aug - 23 Aug
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."
Hopkins Ordinary Bed Breakfast and Ale Works
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 Rp5.841.648
Rp6.297.297 total
includes taxes & fees
25 Aug - 26 Aug
Gay Street Inn
South Court Inn
Front of property

South Court Inn

4.0 star property
10.0 out of 10, Exceptional, (8)
"The family running the inn is a wonderful and young couple preserving the history of the house and creating inclusive and welcoming environment for the guests. "
South Court Inn
Hidden View Bed & Breakfast
Terrace/patio

Hidden View Bed & Breakfast

4.0 star property
Hidden View Bed & Breakfast
Ledge House Bed & Breakfast
Exterior

Ledge House Bed & Breakfast

2.0 star property
10.0 out of 10, Exceptional, (2)
"My husband and I enjoyed our stay very much. It was clean and had a lovely view from the main deck. What really made this house amazing was our hostess, Annie. She was very accommodating. Our breakfast was outstanding. Annie was extremely knowledgeable of the area and the best places to visit and eat. The house has a couple decks that could use some updating and a vine was well on its way to choking out a beautiful large tree near the main deck. Take note that if you’re planning on renting...
Ledge House Bed & Breakfast
The Inn on Thistle Hill
Garden

The Inn on Thistle Hill

2.5 star property
6.2 out of 10, (65)
"This Inn is extremely run-down and poorly maintained. We did not actually check in when we saw the accommmodations. Avoid."
The Inn on Thistle Hill
Purcellville Home
Interior

Purcellville Home

3.5 star property
8.8 out of 10, Excellent, (6)
"This was just what we needed. I appreciated the quiet and Lana was so nice. "
Purcellville Home
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

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"Property Well Maintained"
Robert 1-night trip
Posted 20 hours ago
Fairfield Inn & Suites by Marriott Winchester

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 is a B&B in the surrounding area: 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.