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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 42 B&B in Winchester with updated reviews, rates, and availability.

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 AED 551
AED 628 total
includes taxes & fees
13 May - 14 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 AED 897
AED 1,023 total
includes taxes & fees
21 May - 22 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 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 AED 536
AED 693 total
includes taxes & fees
19 May - 20 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 AED 988
AED 1,080 total
includes taxes & fees
10 Jun - 11 Jun
Glen Gordon Manor
Stone Manor Boutique Inn
Outdoor wedding area

Stone Manor Boutique Inn

3.5 star property
9.6 out of 10, Exceptional, (91)
"It is a quiet and elegant property inside The breakfast was delicious and the owners were friendly and hospitable."
The price is AED 781
AED 891 total
includes taxes & fees
13 May - 14 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 AED 1,142
AED 1,248 total
includes taxes & fees
13 May - 14 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 AED 1,319
AED 1,421 total
includes taxes & fees
15 May - 16 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 AED 1,010
AED 1,315 total
includes taxes & fees
13 May - 14 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 AED 1,194
AED 1,625 total
includes taxes & fees
13 May - 14 May
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Terrace/patio

River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B

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!"
The price is AED 739
AED 1,075 total
includes taxes & fees
22 May - 23 May
River Retreat Suite In Town!- 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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Other property types in Winchester

Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (313)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Outdoor dining

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

9.2 out of 10, Wonderful, (13)
"Week with elderly family members and this home was a good spot to rest and relax. Upon arrival, house was neat and clean. Well stocked with cooking items. Nice layout. Good central locations for day trip options. Overall I would recommend this home. "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"Beautiful location and home"
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
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 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?
Here are some B&Bs in the area: Hillbrook Inn: 9 rooms. 13.5 mi (21.7 km) from the heart of Winchester. 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.