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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

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, (236)
"Stunning property and awesome room. Already booking my next stay in a few weeks with the family!"
The price is SAR 563
SAR 641 total
includes taxes & fees
30 Apr - 1 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 SAR 644
SAR 734 total
includes taxes & fees
30 Apr - 1 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 SAR 702
SAR 794 total
includes taxes & fees
8 May - 9 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 SAR 548
SAR 707 total
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)
"Such a beautiful property. Dinner and breakfast was scrumptious. It is perfect :DC getaway. Highly recommended. "
The price is SAR 897
SAR 980 total
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 SAR 777
SAR 885 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)
"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 SAR 1,128
SAR 1,233 total
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)
"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, (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 SAR 1,347
SAR 1,452 total
includes taxes & fees
1 May - 2 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)
"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 SAR 1,032
SAR 1,339 total
includes taxes & fees
4 May - 5 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. "
The price is SAR 544
SAR 609 total
includes taxes & fees
30 Apr - 1 May
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 SAR 1,219
SAR 1,681 total
includes taxes & fees
6 May - 7 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 SAR 694
SAR 869 total
includes taxes & fees
29 May - 30 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)
"Lovely cabin, very clean and well maintained. A girlfriend weekend and we wanted a great place to hang out and this fit the bill. We never got the TV to work but could be user error. "
The price is SAR 1,084
SAR 1,373 total
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)
"This was absolutely just what we needed! The view was so breathtaking and the serenity of this place is to die for! I was very pleased with our stay here and we will definitely be returning de"
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, (97)
"We had great time fishing, canoeing and sightseeing. We visited Charles Town and went on the night time Ghost Tour. This area is loaded with Civil war history.The fish were hiding but the weather was perfect.Scott was a great host. "
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.