Find the Best Winchester Bed and Breakfast

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Browse Select Winchester B&B

Loudoun Valley Manor
Reception

Loudoun Valley Manor

3.0 star property
9.6 out of 10, Exceptional, (237)
"Stunning property and awesome room. Already booking my next stay in a few weeks with the family!"
The price is £128
includes taxes & fees
4 May - 5 May
Loudoun Valley Manor
Inn at Evergreen
Hallway

Inn at Evergreen

3.5 star property
9.4 out of 10, Exceptional, (123)
"We so enjoyed staying at this inn. We didn’t know it was in a country club with access to several of the amenities of the club. The room was beautiful, the innkeeper was very accommodating and any of the staff we ran into were lovely. A short drive to the closest metro station, we spent a day in DC, & the 2nd day in the rolling hills of northern VA in wine country where we had good wines & enjoyed a lovely dinner at a recommend spot. We would stay here again. "
The price is £216
includes taxes & fees
5 May - 6 May
Inn at Evergreen
The Carriage Inn B&B
Porch

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (416)
"We stayed in the Copper Beech Suite, which was spacious and comfortable. It has its own screened-in porch which was wonderful to sit on at all times of the day. The hosts are very friendly, welcoming and attentive. And the breakfasts were very good. Highly recommended! "
The price is £158
includes taxes & fees
13 May - 14 May
The Carriage Inn B&B
Hillbrook Inn
Premium bedding, desk, iron/ironing board, free WiFi

Hillbrook Inn

4.0 star property
8.6 out of 10, Excellent, (665)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
The price is £141
includes taxes & fees
18 May - 19 May
Hillbrook Inn
Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (83)
"Staff is completely attentive to the guests."
The price is £196
includes taxes & fees
14 May - 15 May
Glen Gordon Manor
Stone Manor Boutique Inn
Outdoor wedding area

Stone Manor Boutique Inn

3.5 star property
9.6 out of 10, Exceptional, (90)
"It is a quiet and elegant property inside The breakfast was delicious and the owners were friendly and hospitable."
The price is £176
includes taxes & fees
18 May - 19 May
Stone Manor Boutique Inn
Lily Garden Bed and Breakfast
Front of property

Lily Garden Bed and Breakfast

2.5 star property
9.6 out of 10, Exceptional, (67)
"These folks are very good communicators and the location is great. The property itself is rather run down and the front steps are certainly not up to code. Very tight inside. Okay for younger travelers but not for older folks. "
Lily Garden Bed and Breakfast
Caravan Suite location Private Lily Garden BnB
Exterior

Caravan Suite location Private Lily Garden BnB

10.0 out of 10, Exceptional, (56)
"Enjoyed a relaxing three week stay with my Dog in a cozy carriage gouse nesled in beautiful historic Harpers Ferry. Owner provided breakfeast and check in weekly to ensure for a comfortable stay. Recommend this location and will stay again if in the area. "
Caravan Suite location Private Lily Garden BnB
Rustic Log cabin bed and breakfast in Virginia wine country
Interior

Rustic Log cabin bed and breakfast in Virginia wine country

8.0 out of 10, Very good, (1)
"A very lovely setting in the woods and beautiful houses throughout the neighborhood. Very peaceful location and unique home."
Rustic Log cabin bed and breakfast in Virginia wine country
South Court Inn
Exterior

South Court Inn

4.0 star property
10.0 out of 10, Exceptional, (7)
"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
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
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
9.8 out of 10, Exceptional, (28)
"Great overnight stay. Brewery on the property. An upscale General store across the street with a cocktail bar and a Pizza Restaurant. Then Copper Fox Distillery, restaurants, shops and antiques right across the bridge. Close to Luray, Culpepper and lots of Wineries. "
The price is £243
includes taxes & fees
6 May - 7 May
Hopkins Ordinary Bed Breakfast and Ale Works
Mayneview B&B
Outdoor spa tub

Mayneview B&B

4.0 star property
8.2 out of 10, Very good, (412)
"Fabulous place to stay, beautiful and clean, delicious breakfast, easy access to Shenandoah National Park, close to the little downtown area. "
Mayneview B&B
Gay Street Inn
Porch

Gay Street Inn

3.5 star property
10.0 out of 10, Exceptional, (32)
"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 £289
includes taxes & fees
8 May - 9 May
Gay Street 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)
"We arrived and the property was CLOSED and under construction. "
The Manor at Courtland Farm
The Van Gogh Room in Villa
Pool

The Van Gogh Room in Villa

9.0 out of 10, Wonderful, (60)
"The host was wonderful! The property was lovely and the area was exceptional! "
The price is £273
includes taxes & fees
3 May - 4 May
The Van Gogh Room in Villa
Cantuta Inn
Beach

Cantuta Inn

3.0 star property
9.0 out of 10, Wonderful, (68)
"The staff was friendly, the room was clean and the location was convenient for what we wanted to do. "
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, (32)
"It is an amazing place with a gorgeous view of the mountains and welcoming host"
The price is £346
includes taxes & fees
4 May - 5 May
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Light Horse Inn: Suite 4
Living area

Light Horse Inn: Suite 4

10.0 out of 10, Exceptional, (11)
"Great all around"
The price is £178
includes taxes & fees
4 May - 5 May
Light Horse Inn: Suite 4
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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Other property types in Winchester

Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"Great cabin. Clean and so welcoming"
The price is £279
includes taxes & fees
7 May - 8 May
Dreamtime - Modern A-frame Cabin w/ Hot tub
Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (312)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Miscellaneous

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (98)
"This was a perfect clean comfortable place to stay while exploring the Harper's Ferry area. Hosts Scott and Margie are friendly and welcoming"
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
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.

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: 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. Hillbrook Inn: 9 rooms. Located 13.5 mi (21.7 km) from the core 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.