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Check prices for these dates

Next weekend
26 Sep - 28 Sep
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

B&B in Winchester

Our top choices for Winchester bed & breakfast

Loudoun Valley Manor
Reception

Loudoun Valley Manor

3.0 star property
9.6 out of 10, Exceptional, (264)
"Very quiet and friendly staff"
The price is SAR 523
SAR 597 total
includes taxes & fees
29 Sep - 30 Sep
Loudoun Valley Manor
The Carriage Inn B&B
Courtyard

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (427)
"Excellent, historic, amazing breakfast and hostess"
The price is SAR 594
SAR 671 total
includes taxes & fees
29 Sep - 30 Sep
The Carriage Inn B&B
Lily Garden Bed and Breakfast
Front of property

Lily Garden Bed and Breakfast

2.5 star property
9.6 out of 10, Exceptional, (74)
"The owners are the sweetest. Easy communication and great breakfast options included!"
Lily Garden Bed and Breakfast
Hillbrook Inn
Property amenity

Hillbrook Inn

4.0 star property
8.6 out of 10, Excellent, (669)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
The price is SAR 694
SAR 871 total
includes taxes & fees
30 Sep - 1 Oct
Hillbrook Inn
Inn at Evergreen
Free daily full breakfast

Inn at Evergreen

3.5 star property
9.4 out of 10, Exceptional, (129)
"Clean,very nice facility "
Inn at Evergreen
Cantuta Inn
Garden

Cantuta Inn

3.0 star property
9.0 out of 10, Wonderful, (71)
"Clean and well taken care of. Owner was friendly and cooked a nice breakfast. A quick walk to the downtown of Harper's Ferry."
The price is SAR 563
SAR 630 total
includes taxes & fees
22 Sep - 23 Sep
Cantuta Inn
The Inn at Grass Roots Hill
Property entrance

The Inn at Grass Roots Hill

3.0 star property
10.0 out of 10, Exceptional, (2)
"House and property are absolutely beautiful. Staff are amazing and super friendly "
The price is SAR 1,678
SAR 1,913 total
includes taxes & fees
27 Sep - 28 Sep
The Inn at Grass Roots Hill
Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (90)
"The location is good."
The price is SAR 1,234
SAR 1,349 total
includes taxes & fees
14 Oct - 15 Oct
Glen Gordon Manor
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
Caravan Suite location Private Lily Garden BnB
Property grounds

Caravan Suite location Private Lily Garden BnB

10.0 out of 10, Exceptional, (60)
"I recommend this place 100 percent"
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, (36)
"It is an amazing place with a gorgeous view of the mountains and welcoming host"
The price is SAR 1,182
SAR 1,642 total
includes taxes & fees
1 Oct - 2 Oct
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Gay Street Inn
Interior detail

Gay Street Inn

3.5 star property
10.0 out of 10, Exceptional, (34)
"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
7 Oct - 8 Oct
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
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, (49)
"This was one of the most beautiful places I have ever stayed. The service was excellent!"
The Manor at Courtland Farm
Stone Manor Boutique Inn
Garden

Stone Manor Boutique Inn

3.5 star property
9.6 out of 10, Exceptional, (93)
"It is a quiet and elegant property inside The breakfast was delicious and the owners were friendly and hospitable."
The price is SAR 815
SAR 929 total
includes taxes & fees
29 Sep - 30 Sep
Stone Manor Boutique Inn
The Van Gogh Room in Villa
Pool

The Van Gogh Room in Villa

9.0 out of 10, Wonderful, (64)
"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 1,097
SAR 1,405 total
includes taxes & fees
1 Oct - 2 Oct
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
10.0 out of 10, Exceptional, (31)
"Great place. Good food, great beer."
Hopkins Ordinary Bed Breakfast and Ale Works
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Dining

Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B

10.0 out of 10, Exceptional, (3)
"Beautiful house. Renovations are not quite complete yet, and the electronic locks needed extra communication with the owner to use, but still a great stay. Perfect location and this place will be gorgeous after renovations are complete."
The price is SAR 815
SAR 1,178 total
includes taxes & fees
21 Sep - 22 Sep
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Dining

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 SAR 858
SAR 1,215 total
includes taxes & fees
21 Sep - 22 Sep
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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Top Winchester Hotel Reviews

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"Great staff"
Dawn 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Winchester

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. 18.2 mi (29.3 km) from the downtown core. Enjoy the designer toiletries and in-room fireplace. Hillbrook Inn: 9 rooms. Situated 13.5 mi (21.7 km) from the heart 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.