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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

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, (227)
"Olga is a wonderful host. This is our second time staying at Loundoun Valley Manor and we enjoyed it as much as the first time. It is a great place to stay. "
The price is SAR 563
SAR 641 total
includes taxes & fees
23 Feb - 24 Feb
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, (64)
"Lily Garden Bed & Breakfast was lovely! Breakfast was delicious, decor was amazing, and the property was safe, quiet, and clean. This is the perfect place to stay when visiting Harpers Ferry. Only about 10 minutes walk from the main part of the historic district. The host was absolutely wonderful, communicative, and friendly."
Lily Garden Bed and Breakfast
The Carriage Inn B&B
Front of property

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (413)
"Had a wonderful weekend staying here. The breakfast was amazing and the rooms were cozy. Would definitely recommend. "
The price is SAR 702
SAR 793 total
includes taxes & fees
6 Mar - 7 Mar
The Carriage Inn B&B
Inn at Evergreen
Front of property

Inn at Evergreen

3.5 star property
9.2 out of 10, Wonderful, (118)
"Great place for a relaxing stay. Very clean and tidy. "
The price is SAR 916
SAR 1,044 total
includes taxes & fees
8 Mar - 9 Mar
Inn at Evergreen
Stone Manor Boutique Inn
Property entrance

Stone Manor Boutique Inn

3.5 star property
9.6 out of 10, Exceptional, (88)
"It was good"
The price is SAR 679
SAR 774 total
includes taxes & fees
9 Mar - 10 Mar
Stone Manor Boutique 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, (56)
"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
Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (82)
"Upon arrival we enjoyed a wonderful greeting and tour from Hayden. The property was everything we were looking for in a getaway stay. All of the staff throughout our stay made us feel very welcome. The dining experience was fantastic. I'm not sure I will ever order duck again unless Chef Dane is in the kitchen and the dining staff for the evening made sure we were taken care of. Thanks again to Michelle for the breakfast prior to our departure. We cant wait to come back !!!"
The price is SAR 746
SAR 816 total
includes taxes & fees
27 Feb - 28 Feb
Glen Gordon Manor
Airwell Bed and Breakfast
Exterior

Airwell Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (36)
"The property is beautiful and the owners charming. I wish I knew about this place sooner."
Airwell Bed and Breakfast
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
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 495
SAR 688 total
includes taxes & fees
23 Mar - 24 Mar
Potomac Room-one bed
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, (661)
"All of the staff are super nice. Breakfast was delicious and our room was clean. Would definitely stay again."
The price is SAR 709
SAR 888 total
includes taxes & fees
25 Mar - 26 Mar
Hillbrook Inn
The Manor at Courtland Farm
Exterior

The Manor at Courtland Farm

3.5 star property
9.2 out of 10, Wonderful, (47)
"This was one of the most beautiful places I have ever stayed. The service was excellent!"
The Manor at Courtland Farm
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, (28)
"Great overnight stay. Brewery on the property. An upscale General store across the street with a cocktail bar and a Pizza Restaurant. Then Copper Fox Distillery, restaurants, shops and antiques right across the bridge. Close to Luray, Culpepper and lots of Wineries. "
The price is SAR 1,046
SAR 1,143 total
includes taxes & fees
24 Feb - 25 Feb
Hopkins Ordinary Bed Breakfast and Ale Works
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
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 1,031
SAR 1,325 total
includes taxes & fees
23 Feb - 24 Feb
The Van Gogh Room in Villa
Cantuta Inn
Front of property

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. "
The price is SAR 563
SAR 630 total
includes taxes & fees
23 Mar - 24 Mar
Cantuta Inn
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
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 SAR 1,219
SAR 1,680 total
includes taxes & fees
23 Feb - 24 Feb
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
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
Gay Street Inn
Room

Gay Street Inn

3.5 star property
10.0 out of 10, Exceptional, (31)
"Drew was a great host and was shared options for dining locally and understands how a first impression can set the tone of the stay. His attitude was very appreciated."
The price is SAR 1,346
SAR 1,451 total
includes taxes & fees
27 Feb - 28 Feb
Gay Street Inn
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

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Riverview from covered deck area

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (340)
"My friend and I spent the weekend in John's Cozy Cabin to enjoy some time away from our urban settings and focus on writing in a quiet, secluded place. This cabin was just what we were seeking because it was tranquil, isolated, in serene settings in the forest along the Shenandoah River, and it had everything we needed. John was proactive in his approach, taking the time to discuss our needs and preferences before our stay. His thorough communication and attention to detail ensured that my...
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Exterior

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

10.0 out of 10, Exceptional, (304)
"Quiet and the hot tub was popular. Nice winter trip through Shen Nat Park, but no snowshoeing."
The price is SAR 656
SAR 1,098 total
includes taxes & fees
23 Feb - 24 Feb
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (36)
"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub, "
Dreamtime - Modern A-frame Cabin w/ 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?
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. Located 13.5 mi (21.7 km) from the core 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 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.