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Compare 37 B&B in Winchester with updated reviews, rates, and availability.

Maria's Garden and Inn
3.0 star property
9.2 out of 10, Wonderful, (103)
"Unique experience, we enjoyed the personalized service."
The price is AED 514
AED 627 total
includes taxes & fees
11 Jun - 12 Jun
Maria's Garden and Inn
Loudoun Valley Manor
3.0 star property
9.6 out of 10, Exceptional, (186)
"The Loudon Valley Manor is the most perfect place for a cute little get away. My boyfriend and I stayed here while in town for a wedding and we were amazed by the beauty of the property and the kindness and hospitality shown to us by Olga. We arrived late and left early and Olga was entirely understanding and helpful the whole time. I highly recommend staying here!"
The price is AED 503
AED 574 total
includes taxes & fees
10 Jun - 11 Jun
Loudoun Valley Manor
Inn at Evergreen
3.5 star property
9.2 out of 10, Wonderful, (102)
"The room was really well-appointed (320), the property is beautiful. Breakfast was good and it was great to have it included in the stay. Hanna was communicative and helpful. Check-in and check-out were easy. Would stay again"
The price is AED 935
AED 1,065 total
includes taxes & fees
11 Jun - 12 Jun
Inn at Evergreen
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Hillbrook Inn
4.0 star property
8.6 out of 10, Excellent, (658)
"My husband and I wanted a quiet place to decompress. Hillbrook Inn was a perfect place. It was so quiet and in nature. The food at the Inn was also excellent. Definitely will recommend this inn to anyone just to do nothing and be in nature. "
The price is AED 636
AED 802 total
includes taxes & fees
17 Jun - 18 Jun
Hillbrook Inn
The Carriage Inn B&B
3.5 star property
9.6 out of 10, Exceptional, (399)
"Carriage Inn is beautifully maintained. The landscaping is a great bonus. The inn is a wonderful place to relax and enjoy the surroundings."
The price is AED 674
AED 754 total
includes taxes & fees
10 Jun - 11 Jun
The Carriage Inn B&B
Stone Manor Boutique Inn
3.5 star property
9.6 out of 10, Exceptional, (79)
"Very courteous staff, really friendly innkeepers. Would be happy to stay here again!"
The price is AED 760
AED 867 total
includes taxes & fees
10 Jun - 11 Jun
Stone Manor Boutique Inn
Lily Garden Bed and Breakfast
2.5 star property
9.6 out of 10, Exceptional, (48)
"Loved it! Would totally stay again. "
Lily Garden Bed and Breakfast
Mayneview B&B
4.0 star property
8.0 out of 10, Very Good, (402)
"Charming & peaceful B&B with friendly hosts & delicious breakfast! Very comfortable bed & linens. The hot tub & fire pit are an added bonus. I could never get tired of the views. Downtown Luray is within walking distance & the National Park is a beautiful 15 minute drive. You won’t be disappointed! "
Mayneview B&B
Glen Gordon Manor
3.5 star property
9.8 out of 10, Exceptional, (81)
"Great experience. Beautiful site. "
Glen Gordon Manor
Potomac Room-one bed
10.0 out of 10, Exceptional, (2)
"This was a great location close to everything. The room was comfortable and clean. The owner was very friendly and accommodating."
The price is AED 485
AED 654 total
includes taxes & fees
11 Jun - 12 Jun
Potomac Room-one bed
Cantuta Inn
3.0 star property
8.8 out of 10, Excellent, (63)
"Quick overnight while traveling westbound. Pleasant and informative host couple. Healthy breakfast and good coffee / tea! Clean, quiet accomodations. "
The price is AED 507
AED 568 total
includes taxes & fees
10 Jun - 11 Jun
Cantuta Inn
The Van Gogh Room in Villa
8.8 out of 10, Excellent, (56)
"Villa Maude is an exquisite jewel nestled in Virginia's "horse country" with a panoramic view of the Blue Ridge Mountains. I stayed in the Van Gogh room, and it was most comfortable. The host, Maude, was very accommodating. Darla, the dog, after a couple of obligatory barks (dutifully protecting the manse) was a real sweetheart. I was staying there to attend a social function nearby but have this place on my list to return to for more of an R&R stay. Quality always speaks for itself and this...
The price is AED 918
AED 1,177 total
includes taxes & fees
10 Jun - 11 Jun
The Van Gogh Room in Villa
Airwell Bed and Breakfast
4.0 star property
10.0 out of 10, Exceptional, (30)
"My stay at Airwell B&B was exceptional! "
The price is AED 723
AED 824 total
includes taxes & fees
10 Jun - 11 Jun
Airwell Bed and Breakfast
South Court Inn
4.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful historical 4 bedroom bed & breakfast. Traditional bed and breakfast with a 3 course breakfast meal provided at 9am. "
South Court Inn
Smithfield Farm B&B
3.0 star property
9.4 out of 10, Exceptional, (90)
"Beautiful property, beautiful farm and great old House. Farm store right next by was great also. However, no TV in our room and the TV downstairs wasn’t working, also no WiFi at all. I understand getting away from it all in the beautiful country, but to have no internet was disappointing. The breakfast was made and left in fridge before we arrived. It was a tasty plate of cold cuts, fruit , cheeses. A nice hot breakfast featuring eggs and meats from their farm would have been a lot more fun. ...
The price is AED 798
AED 881 total
includes taxes & fees
10 Jun - 11 Jun
Smithfield Farm B&B
The Manor at Courtland Farm
3.5 star property
9.4 out of 10, Exceptional, (46)
"This was one of the most beautiful places I have ever stayed. The service was excellent!"
The Manor at Courtland Farm
Caravan Suite location Private Lily Garden BnB
10.0 out of 10, Exceptional, (47)
"Nice location for a long weekend in Harper’s Ferry area. Makes a nice base to explore."
Caravan Suite location Private Lily Garden BnB
Belle Meade Bed and Breakfast
2.5 star property
9.6 out of 10, Exceptional, (34)
"Wonderful B and B, owners/operators went out of thier way to make us feel comfortable. Beautiful, quiet and peaceful setting with a great view of Old Rag mountain!"
The price is AED 845
AED 923 total
includes taxes & fees
10 Jun - 11 Jun
Belle Meade Bed and Breakfast
Inn of the Shenandoah
4.0 star property
9.8 out of 10, Exceptional, (34)
"Art was super helpful from the second of our arrival to our departure. He helped provide a wonderful memory. The next time I travel to that area - I'm staying there!"
Inn of the Shenandoah
Light Horse Inn: Suite 4
9.8 out of 10, Exceptional, (8)
"Great location and breakfast. The furnishings need upgrade."
The price is AED 680
AED 860 total
includes taxes & fees
16 Jun - 17 Jun
Light Horse Inn: Suite 4
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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.

Other property types in Winchester

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (190)
"My family and I stayed with our dog at this beautiful cabin. It was spacious and decorated so nicely. Very cozy and relaxing atmosphere! We will definitely be back."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (26)
"Cabin was amazing. Definitely would go back!"
The price is AED 1,359
AED 1,705 total
includes taxes & fees
6 Jul - 7 Jul
Dreamtime - Modern A-frame Cabin w/ Hot tub
Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (50)
"We had a great time. Cabin was clean, spacious and well maintained. The fire pit and hot tub were what we looked forward to the most... We were not disappointed."
Hidden Gem in the woods with hot tub
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. Theater nuts will enjoy catching a show at Bright Box Theater or Winchester Little Theater while in Winchester.
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.
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 explore some cultural attractions on your trip, Museum of the Shenandoah Valley and Bright Box Theater are worthy sites to check out. You might put Shenandoah Valley Discovery Museum and Jim Barnett Park 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.

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