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Compare 40 B&B in Winchester with updated reviews, rates, and availability.

Loudoun Valley Manor
Aerial view

Loudoun Valley Manor

3.0 star property
9.6 out of 10, Exceptional, (219)
"Pleasant , comfortable and Olga was friendly and very helpful and made the best omelettes! "
The price is SAR 563
SAR 642 total
includes taxes & fees
23 Dec - 24 Dec
Loudoun Valley Manor
Lily Garden Bed and Breakfast
Front of property

Lily Garden Bed and Breakfast

2.5 star property
9.6 out of 10, Exceptional, (61)
"I enjoyed the rustic experience of being in a barn. The barn had lots of wooden paneling. The little pond and chairs outside were nice to sit and read. Most importantly, the location was close to hiking trails and restaurant. The owner was very quick to respond to texts and offer recommendations. "
Lily Garden Bed and Breakfast
Stone Manor Boutique Inn
Property entrance

Stone Manor Boutique Inn

3.5 star property
9.6 out of 10, Exceptional, (84)
"This b&b was beautiful, elegant but extremely comfortable. We did not want to leave. Our hosts were fabulous and allowed us access to the entire property including a stunning dining area and a tavern. Our dogs loved it!! Lovely garden area and grounds in general. The inside was stunning with unusual and eclect furniture. Would highly recommend this place. Not much area but Doordash did the trick! Luxurious bedding"
The price is SAR 756
SAR 862 total
includes taxes & fees
23 Dec - 24 Dec
Stone Manor Boutique Inn
The Carriage Inn B&B
Front of property

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (412)
"Had a wonderful weekend staying here. The breakfast was amazing and the rooms were cozy. Would definitely recommend. "
The price is SAR 703
SAR 795 total
includes taxes & fees
2 Jan - 3 January 2025
The Carriage Inn B&B
Inn at Evergreen
Front of property

Inn at Evergreen

3.5 star property
9.2 out of 10, Wonderful, (116)
"Great place for a relaxing stay. Very clean and tidy. "
The price is SAR 816
SAR 930 total
includes taxes & fees
2 Jan - 3 January 2025
Inn at Evergreen
Maria's Garden and Inn
Room

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
Hillbrook Inn
Front of property

Hillbrook Inn

4.0 star property
8.6 out of 10, Excellent, (660)
"All of the staff are super nice. Breakfast was delicious and our room was clean. Would definitely stay again."
The price is SAR 695
SAR 873 total
includes taxes & fees
5 Jan - 6 January 2025
Hillbrook Inn
Cantuta Inn
Front of property

Cantuta Inn

3.0 star property
9.0 out of 10, Wonderful, (67)
"The staff was friendly, the room was clean and the location was convenient for what we wanted to do. "
The price is SAR 487
SAR 545 total
includes taxes & fees
23 Dec - 24 Dec
Cantuta Inn
Caravan Suite location Private Lily Garden BnB
Our Family Cottage. The Suite is the second and third stories of the building.

Caravan Suite location Private Lily Garden BnB

10.0 out of 10, Exceptional, (55)
"We enjoyed the quiet location, yet it was close enough to the lower town to walk to everything we wanted to see. The suite was well-furnished and comfortable. The breakfast items were provided in very generous amounts. All the directions and information provided were easy to follow and use."
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
Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (81)
"Great experience. Beautiful site. "
The price is SAR 785
SAR 858 total
includes taxes & fees
7 Jan - 8 January 2025
Glen Gordon Manor
Potomac Room-one bed
1

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 SAR 496
SAR 684 total
includes taxes & fees
23 Dec - 24 Dec
Potomac Room-one bed
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 1,033
SAR 1,340 total
includes taxes & fees
23 Dec - 24 Dec
The Van Gogh Room in Villa
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
South Court Inn
Exterior

South Court Inn

4.0 star property
10.0 out of 10, Exceptional, (6)
"The family running the inn is a wonderful and young couple preserving the history of the house and creating inclusive and welcoming environment for the guests. "
South Court Inn
Hopkins Ordinary Bed Breakfast and Ale Works
Garden

Hopkins Ordinary Bed Breakfast and Ale Works

3.0 star property
9.8 out of 10, Exceptional, (27)
"Beautiful comfortable room with porch swing for afternoon and late evening relaxing. Tasty breakfast. Beer/ale tasting room in the basement. Thornton River walk steps away. Innkeepers Sherrie and Kevin do it all. We had a wonderful time there and will come back. "
The price is SAR 1,122
SAR 1,227 total
includes taxes & fees
2 Jan - 3 January 2025
Hopkins Ordinary Bed Breakfast and Ale Works
The Manor at Courtland Farm
Exterior

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 price is SAR 1,011
SAR 1,152 total
includes taxes & fees
5 Jan - 6 January 2025
The Manor at Courtland Farm
Belle Meade Bed and Breakfast
Front of property

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!"
Belle Meade Bed and Breakfast
Airwell Bed and Breakfast
Exterior

Airwell Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (34)
"An absolutely beautiful place that was so comfortable that you didn't want to leave. The breakfasts were super yummy and filling. Lisa and Todd were so welcoming and you can tell that they love running a BnB!!! We had such a wonderful stay and look forward to returning 😍"
The price is SAR 770
SAR 878 total
includes taxes & fees
23 Dec - 24 Dec
Airwell Bed and Breakfast
Mayneview B&B
Exterior

Mayneview B&B

4.0 star property
8.2 out of 10, Very Good, (409)
"Fantastic setting beautiful home "
Mayneview 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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Other property types in Winchester

Hidden Gem in the woods with hot tub
Exterior

Hidden Gem in the woods with hot tub

9.6 out of 10, Exceptional, (66)
"Nice"
Hidden Gem in the woods with hot tub
Secluded, Cozy Cottage in the Shenandoah Valley
Quiet nights and so many stars.

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (162)
"It's the perfect cozy place for two for Thanksgiving. The indoor fireplace has plenty of firewood, and the outdoor firepit has a grill plate, perfect for making smores. We started our mornings having coffee in the hot tub. We will stay here again! "
Secluded, Cozy Cottage in the Shenandoah Valley
Terra Alta - Incredible River Views and Hot Tub!
Soak in the tub while enjoying the beautiful view of the river below!

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
The price is SAR 1,044
SAR 2,437 total
includes taxes & fees
26 Dec - 27 Dec
Terra Alta - Incredible River Views and 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. If your ideal vacation to Winchester includes spending lots of time outside, Jim Barnett Park and Frederick Douglass Park 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?
You might try out one of these options if you’re looking for an accommodation that offers free breakfast: La Quinta Inn & Suites by Wyndham WinchesterMicrotel Inn & Suites by Wyndham WinchesterComfort Inn & SuitesCountry Inn & Suites by Radisson, Winchester, VA
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 Frederick Douglass Park 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.