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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

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, (231)
"Thank you Olga for a wonderful stay!"
The price is AED 551
AED 628 total
includes taxes & fees
13 Apr - 14 Apr
Loudoun Valley Manor
Inn at Evergreen
Hallway

Inn at Evergreen

3.5 star property
9.2 out of 10, Wonderful, (122)
"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 605
AED 690 total
includes taxes & fees
14 Apr - 15 Apr
Inn at Evergreen
The Carriage Inn B&B
Porch

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (415)
"Fantastic"
The price is AED 833
AED 941 total
includes taxes & fees
11 Apr - 12 Apr
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, (662)
"I stayed at the Hawthorne House. A beautiful property, close to Summit Point and the Race Track. My room, East, was gorgeous. I loved my stay."
The price is AED 504
AED 656 total
includes taxes & fees
28 Apr - 29 Apr
Hillbrook Inn
Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (82)
"Upon arrival we enjoyed a wonderful greeting and tour from Hayden. The property was everything we were looking for in a getaway stay. All of the staff throughout our stay made us feel very welcome. The dining experience was fantastic. I'm not sure I will ever order duck again unless Chef Dane is in the kitchen and the dining staff for the evening made sure we were taken care of. Thanks again to Michelle for the breakfast prior to our departure. We cant wait to come back !!!"
The price is AED 731
AED 799 total
includes taxes & fees
29 Apr - 30 Apr
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 AED 760
AED 867 total
includes taxes & fees
23 Apr - 24 Apr
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, (66)
"Lily Garden Bed & Breakfast was lovely! Breakfast was delicious, decor was amazing, and the property was safe, quiet, and clean. This is the perfect place to stay when visiting Harpers Ferry. Only about 10 minutes walk from the main part of the historic district. The host was absolutely wonderful, communicative, and friendly."
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)
"This was one of the most charming bed-and-breakfast stays that we have ever had. Shannon and Joe were wonderful hosts who clearly cared for the comfort and quality experience of their guests. Breakfast each morning was amazing and bursting with creativity and flavor! Our room was beautifully decorated with a very comfortable bed. Caution: bedroom walls are a little thin, so you may hear and be heard during your stay!"
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)
"My fiancé and i had a wonderful time here. right in the heart of Berkley Springs, is is convenient to shopping, galleries and the famous hot springs. Tom was a 5-star host! He greeted us at the door, guided us to room and couldn't have been nicer, more friendly or professional. We both felt like family here. The room was elegant, with a gas fireplace, comfortable four-poster bed, and private bath. Breakfast was wonderful, off a patio where Tom grows some of the veggies that find their...
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 1,086
AED 1,188 total
includes taxes & fees
14 Apr - 15 Apr
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)
"Had a lovely weekend stay at Mayneview B&B. The space was cozy and beautifully decorated. I was very impressed by the cleanliness and the great hospitality of inn keeper Gregory. I’d highly recommend a stay here if you’re visiting the area. "
Mayneview B&B
Gay Street Inn
Porch

Gay Street Inn

3.5 star property
10.0 out of 10, Exceptional, (31)
"Drew was a great host and was shared options for dining locally and understands how a first impression can set the tone of the stay. His attitude was very appreciated."
The price is AED 1,319
AED 1,421 total
includes taxes & fees
14 Apr - 15 Apr
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)
"Art is a wonderful host. It was a great Inn and we will go again "
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)
"Good stay. Beautiful view. Having never been to Purceville, I was taken aback by the fact that the establishment on s dirt road. "
The price is AED 1,010
AED 1,306 total
includes taxes & fees
11 Apr - 12 Apr
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. "
The price is AED 533
AED 597 total
includes taxes & fees
13 Apr - 14 Apr
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 1,654 total
includes taxes & fees
11 Apr - 12 Apr
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 AED 680
AED 871 total
includes taxes & fees
14 Apr - 15 Apr
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

Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (310)
"This lovely cabin was exactly what we were looking for. It's cozy with a spectacular view and the river access was perfectly scenic. "
Star view cabin-Riverfront
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)
"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub, "
The price is AED 1,062
AED 1,329 total
includes taxes & fees
24 Apr - 25 Apr
Dreamtime - Modern A-frame Cabin w/ Hot tub
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, (95)
"We stayed for 2 nights fishing, and site seeing get away. It was the perfect location!"
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 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. 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 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.