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Check prices for these dates

Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb
In one month
20 Feb - 22 Feb
In two months
20 Mar - 22 Mar

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 all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is AED 1,025
AED 1,120 total
includes taxes & fees
18 Feb - 19 Feb
Glen Gordon Manor
Exterior

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 AED 42,240
AED 54,515 total
includes taxes & fees
27 Jan - 28 Jan
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Front of property

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (674 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is AED 578
AED 739 total
includes taxes & fees
26 Jan - 27 Jan
Hillbrook Inn
Reception

Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (279 reviews)
"Great location for visiting wineries"
United States
Anne
The price is AED 518
AED 590 total
includes taxes & fees
29 Jan - 30 Jan
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
Inn at Evergreen
Front of property

Stone Manor Boutique Inn

Stone Manor Boutique Inn
3.5 star property
Lovettsville
9.6 out of 10, Exceptional, (96 reviews)
"The breakfast was fabulous and the room great "
United States
MICHEL
The price is AED 703
AED 802 total
includes taxes & fees
27 Jan - 28 Jan
Stone Manor Boutique Inn
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 AED 798
AED 1,118 total
includes taxes & fees
22 Feb - 23 Feb
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
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 AED 569
AED 638 total
includes taxes & fees
26 Jan - 27 Jan
Cantuta Inn
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, (32 reviews)
"Great place. Good food, great beer."
United States
Phil
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
9.2 out of 10, Wonderful, (7 reviews)
"House and property are absolutely beautiful. Staff are amazing and super friendly "
United States
Chad
The price is AED 1,652
AED 1,883 total
includes taxes & fees
24 Jan - 25 Jan
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 AED 1,319
AED 1,421 total
includes taxes & fees
29 Jan - 30 Jan
Gay Street Inn
Front of property

Inn of the Shenandoah

Inn of the Shenandoah
4.0 star property
Luray
9.8 out of 10, Exceptional, (40 reviews)
"It was an awesome place to stay!!"
United States
Eileen
The price is AED 1,111
AED 1,337 total
includes taxes & fees
27 Jan - 28 Jan
Inn of the Shenandoah
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, (441 reviews)
"Excellent accommodations and breakfast. "
United States
William
The price is AED 471
AED 533 total
includes taxes & fees
28 Jan - 29 Jan
The Carriage 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 AED 756
AED 1,067 total
includes taxes & fees
22 Feb - 23 Feb
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Exterior

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

50's Drive-In Inside the Grand Castalian Inn B&B
Berkeley Springs
The price is AED 841
AED 1,186 total
includes taxes & fees
22 Feb - 23 Feb
50's Drive-In Inside the Grand Castalian 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 AED 672
AED 987 total
includes taxes & fees
25 Jan - 26 Jan
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
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 AED 1,102
AED 1,419 total
includes taxes & fees
24 Jan - 25 Jan
The Van Gogh Room in Villa
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 AED 1,286
AED 1,721 total
includes taxes & fees
24 Jan - 25 Jan
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Clean room. Friendly and helpful staff."
Richard 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester

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: Hillbrook Inn: 9 rooms. 13.5 mi (21.7 km) from the downtown core. Enjoy the free full breakfast and fitness center. The Carriage Inn B&B: 7 rooms. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the designer toiletries and in-room fireplace.
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.