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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

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

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 756
AED 939 total
includes taxes & fees
9 Jun - 10 Jun
Hillbrook Inn
Loudoun Valley Manor
Reception

Loudoun Valley Manor

3.0 star property
9.6 out of 10, Exceptional, (245)
"Loved this place so much I came back with my family. Absolutely recommend for anyone on the road or looking to make a nice little trip to the Virginia countryside. "
The price is AED 490
AED 559 total
includes taxes & fees
9 Jun - 10 Jun
Loudoun Valley Manor
The Carriage Inn B&B
Porch

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (417)
"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
Inn at Evergreen
Hallway

Inn at Evergreen

3.5 star property
9.4 out of 10, Exceptional, (123)
"Wonderful place to stay"
The price is AED 564
AED 643 total
includes taxes & fees
10 Jun - 11 Jun
Inn at Evergreen
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
Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (86)
"Very nice one night stay on a historic property. Very nice common areas. Very relaxing. Good service. Nice breakfast."
The price is AED 915
AED 1,000 total
includes taxes & fees
9 Jun - 10 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 703
AED 802 total
includes taxes & fees
18 Jun - 19 Jun
Stone Manor Boutique Inn
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
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 1,319 total
includes taxes & fees
6 Jun - 7 Jun
The Van Gogh Room in Villa
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, (29)
"Great place. Good food, great beer."
The price is AED 1,086
AED 1,187 total
includes taxes & fees
9 Jun - 10 Jun
Hopkins Ordinary Bed Breakfast and Ale Works
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
Maria's Garden and Inn
Exterior detail

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
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
11 Jun - 12 Jun
Gay Street Inn
Mayneview B&B
Outdoor spa tub

Mayneview B&B

4.0 star property
8.2 out of 10, Very Good, (413)
"Fabulous place to stay, beautiful and clean, delicious breakfast, easy access to Shenandoah National Park, close to the little downtown area. "
Mayneview B&B
South Court Inn
Interior

South Court Inn

4.0 star property
10.0 out of 10, Exceptional, (8)
"The gourmet breakfasts truly were that! The hosts cannot be more gracious. Afternoon snacks and welcome wine are terrific. The grounds and building are beautiful and we could walk to everywhere in town. Lovely experience."
South Court 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
Caravan Suite location Private Lily Garden BnB
Exterior

Caravan Suite location Private Lily Garden BnB

10.0 out of 10, Exceptional, (57)
"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
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 1,646 total
includes taxes & fees
6 Jun - 7 Jun
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 798
AED 1,150 total
includes taxes & fees
29 Jun - 30 Jun
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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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.