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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Winchester

Exterior
Glen Gordon Manor
Glen Gordon Manor
3.5 star property
9.8 out of 10, Exceptional, (90)
"The location is good."
United States
Danny
The price is AED 915
AED 1,000 total
includes taxes & fees
5 Nov - 6 Nov
Glen Gordon Manor
Property amenity
Hillbrook Inn
Hillbrook Inn
4.0 star property
8.6 out of 10, Excellent, (670)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
The price is AED 618
AED 784 total
includes taxes & fees
29 Oct - 30 Oct
Hillbrook Inn
Reception
Loudoun Valley Manor
Loudoun Valley Manor
3.0 star property
9.6 out of 10, Exceptional, (271)
"Great location for visiting wineries"
United States
Anne
The price is AED 507
AED 578 total
includes taxes & fees
5 Nov - 6 Nov
Loudoun Valley Manor
Free daily full breakfast
Inn at Evergreen
Inn at Evergreen
3.5 star property
9.4 out of 10, Exceptional, (131)
"Clean,very nice facility "
United States
Matthew P
Inn at Evergreen
Garden
Stone Manor Boutique Inn
Stone Manor Boutique Inn
3.5 star property
9.6 out of 10, Exceptional, (95)
"The staff, including the owners, were polite and courteous. If we needed anything it was brought expeditiously. The hot tub was a little small but delightful. The fireplace was a nice added touch. We looked forward to each breakfast - simply wonderful. "
United States
Aaron
The price is AED 798
AED 910 total
includes taxes & fees
27 Oct - 28 Oct
Stone Manor Boutique Inn
Family House, Multiple Beds, Balcony, Garden Area | Balcony
Hopkins Ordinary Bed Breakfast and Ale Works
Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
10.0 out of 10, Exceptional, (31)
"Great place. Good food, great beer."
United States
Phil
Hopkins Ordinary Bed Breakfast and Ale Works
Exterior
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
2.0 star property
10.0 out of 10, Exceptional, (1)
"Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend."
United States
Lukas D.
The price is AED 6,484
AED 8,687 total
includes taxes & fees
2 Nov - 3 Nov
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Garden
Cantuta Inn
Cantuta Inn
3.0 star property
9.0 out of 10, Wonderful, (73)
"A comfortable, quiet, & beautiful place to stay. Staff was friendly and able to recommend somewhere good for dinner. "
United States
Aleta
The price is AED 606
AED 679 total
includes taxes & fees
27 Oct - 28 Oct
Cantuta Inn
Property entrance
The Inn at Grass Roots Hill
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 "
United States
Chad
The price is AED 1,685
AED 1,921 total
includes taxes & fees
25 Oct - 26 Oct
The Inn at Grass Roots Hill
Interior detail
Gay Street Inn
Gay Street Inn
3.5 star property
10.0 out of 10, Exceptional, (34)
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
The price is AED 1,319
AED 1,421 total
includes taxes & fees
29 Oct - 30 Oct
Gay Street Inn
Dining
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
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!"
United States
Deirdre A.
The price is AED 798
AED 1,150 total
includes taxes & fees
9 Nov - 10 Nov
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Courtyard
The Carriage Inn B&B
The Carriage Inn B&B
3.5 star property
9.6 out of 10, Exceptional, (432)
"Excellent accommodations and breakfast. "
United States
William
The price is AED 582
AED 657 total
includes taxes & fees
27 Oct - 28 Oct
The Carriage Inn B&B
Outdoor pool
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
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"
United States
Tatiana
The price is AED 1,286
AED 1,784 total
includes taxes & fees
26 Oct - 27 Oct
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Pool
The Van Gogh Room in Villa
The Van Gogh Room in Villa
9.0 out of 10, Wonderful, (66)
"Nice rooms, beautiful property, accommodating host. The pool and gardens are serene and relaxing. Easy drive to many local restaurants, winery’s, breweries…. Close to the AT for those looking to recovery from hiking "
United States
Darla B.
The price is AED 1,194
AED 1,549 total
includes taxes & fees
26 Oct - 27 Oct
The Van Gogh Room in Villa
Dining
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
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."
United States
Daniel F.
The price is AED 714
AED 1,043 total
includes taxes & fees
2 Nov - 3 Nov
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Dining
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Appalachian Suite In Town!- The Grand Castalian Inn B&B
10.0 out of 10, Exceptional, (2)
"We loved the spot and will be back!"
United States
Seth W.
The price is AED 756
AED 1,098 total
includes taxes & fees
2 Nov - 3 Nov
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Dining
50's Drive-In Inside the Grand Castalian Inn B&B
50's Drive-In Inside the Grand Castalian Inn B&B
2.0 star property
The price is AED 798
AED 1,154 total
includes taxes & fees
2 Nov - 3 Nov
50's Drive-In 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

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

10/10 Excellent
"The place was great. Only complaint I have is the towels, they were very scratchy."
Samantha 1-night trip
Posted 20 hours ago
SpringHill 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. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the designer toiletries and in-room fireplace. Hillbrook Inn: 9 rooms. 13.5 mi (21.7 km) from the heart of downtown. 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.