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Check prices for these dates

Next weekend
20 Feb - 22 Feb
In two weeks
27 Feb - 1 Mar
In one month
13 Mar - 15 Mar
In two months
10 Apr - 12 Apr

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 HK$2,259
HK$2,470 total
includes taxes & fees
25 Feb - 26 Feb
Glen Gordon Manor
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 HK$1,168
HK$1,504 total
includes taxes & fees
16 Feb - 17 Feb
Hillbrook Inn
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
Garden view

Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (282 reviews)
"Beatiful Location Reasonable Rates Great Breakfast"
United States
Albert
The price is HK$1,079
HK$1,231 total
includes taxes & fees
12 Feb - 13 Feb
Loudoun Valley Manor
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 HK$1,496
HK$1,706 total
includes taxes & fees
12 Feb - 13 Feb
Stone Manor Boutique Inn
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 HK$1,609
HK$2,303 total
includes taxes & fees
19 Feb - 20 Feb
Appalachian Suite In Town!- The Grand Castalian Inn B&B
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
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 HK$1,349
HK$1,511 total
includes taxes & fees
16 Feb - 17 Feb
Cantuta Inn
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 HK$3,586
HK$4,088 total
includes taxes & fees
17 Feb - 18 Feb
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 HK$2,807
HK$3,026 total
includes taxes & fees
11 Mar - 12 Mar
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 HK$2,365
HK$2,845 total
includes taxes & fees
12 Feb - 13 Feb
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 HK$1,212
HK$1,370 total
includes taxes & fees
16 Feb - 17 Feb
The Carriage Inn B&B
Gazebo

Mayneview B&B

Mayneview B&B
4.0 star property
Luray
8.2 out of 10, Very good, (416 reviews)
"We came to Lurray to see fall foliage and explore the caverns but the real star of our stay was this B&B. What an amazing experience! Gregory was the sweetest human and a great coversationalist. There is a lot of love that has gone into maintaining this old house and it shows. They have crafted a wonderfully curated experience from start to finish. We enjoyed hot chocolates by the fire pit, excellent balanced breakfasts, and a very comfortable king bedroom. 10/10!"
United States
Samantha
The price is HK$1,750
HK$2,018 total
includes taxes & fees
19 Feb - 20 Feb
Mayneview 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 HK$1,609
HK$2,303 total
includes taxes & fees
17 Feb - 18 Feb
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 HK$2,345
HK$3,038 total
includes taxes & fees
12 Feb - 13 Feb
The Van Gogh Room in Villa
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 HK$1,699
HK$2,422 total
includes taxes & fees
17 Feb - 18 Feb
River Retreat Suite In Town!- Inside 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 HK$1,789
HK$2,532 total
includes taxes & fees
19 Feb - 20 Feb
50's Drive-In Inside the Grand Castalian Inn B&B
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 HK$2,735
HK$3,796 total
includes taxes & fees
12 Feb - 13 Feb
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
"Staff was very courteous and friendly throught our entire stay! Everything was updated and very clean. Kids LOVED the pool and breakfast."
Alden 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
1,294
Accommodation
34 B&B
Lowest Price
HK$1,231
Highest Price
HK$4,088

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 are some well-liked B&Bs in the surrounding area: Hillbrook Inn: 9 rooms. 13.5 mi (21.7 km) from the city centre. Enjoy the free full breakfast and fitness centre. 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.
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.

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