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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

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, (94)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is AED 1,172
AED 1,281 total
includes taxes & fees
7 Jan - 8 January 2026
Glen Gordon Manor
Property amenity
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 AED 644
AED 813 total
includes taxes & fees
11 Dec - 12 Dec
Hillbrook Inn
Free daily full breakfast
Inn at Evergreen

Inn at Evergreen

3.5 star property
Haymarket
9.4 out of 10, Exceptional, (131)
"Clean,very nice facility "
United States
Matthew P
Inn at Evergreen
Reception
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 AED 523
AED 597 total
includes taxes & fees
18 Dec - 19 Dec
Loudoun Valley Manor
Garden
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 AED 703
AED 802 total
includes taxes & fees
10 Dec - 11 Dec
Stone Manor Boutique Inn
Family House, Multiple Beds, Balcony, Garden Area | Balcony
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
Property entrance
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 AED 1,685
AED 1,921 total
includes taxes & fees
10 Dec - 11 Dec
The Inn at Grass Roots Hill
Exterior
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 AED 6,483
AED 8,666 total
includes taxes & fees
14 Dec - 15 Dec
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Garden
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 AED 588
AED 658 total
includes taxes & fees
14 Dec - 15 Dec
Cantuta Inn
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

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 AED 714
AED 1,039 total
includes taxes & fees
14 Dec - 15 Dec
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Interior detail
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 AED 1,319
AED 1,421 total
includes taxes & fees
1 Jan - 2 January 2026
Gay Street Inn
Courtyard
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 AED 457
AED 516 total
includes taxes & fees
15 Dec - 16 Dec
The Carriage Inn B&B
Outdoor pool
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view

Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool 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 AED 1,285
AED 1,771 total
includes taxes & fees
10 Dec - 11 Dec
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Pool
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 AED 1,102
AED 1,436 total
includes taxes & fees
1 Jan - 2 January 2026
The Van Gogh Room in Villa
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

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 AED 714
AED 1,039 total
includes taxes & fees
14 Dec - 15 Dec
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Dining
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 AED 756
AED 1,094 total
includes taxes & fees
14 Dec - 15 Dec
Appalachian Suite In Town!- 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

2.0 star property
Berkeley Springs
The price is AED 798
AED 1,146 total
includes taxes & fees
14 Dec - 15 Dec
50's Drive-In Inside 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.
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Top Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Great hotel!"
CHARLES 1-night trip
Posted 2 days ago
The George Washington Hotel, A Wyndham Grand Hotel

Frequently asked questions

Searching for B&Bs in Winchester?
Whether you're on a romantic vacation and want to stay somewhere quiet, or you're traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many types of vacationers. If your ideal vacation 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 its own unique feel. Whether it's a picturesque garden or a sunlit breakfast nook, the small details are what make bed and breakfasts a fun place to get away.
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 downtown core. 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 center.
When is the best time to stay at a B&B in Winchester?
When you're planning your escape to Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What is there to do in Winchester?
Travelers who want to experience Winchester should check out 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 might 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?
You can map out your trip in and around Winchester ahead of time 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. You can also search for flights into Washington Dulles Intl. Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.