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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Winchester bed & breakfast

A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.

1. Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
10.0 out of 10, Exceptional, (99 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
The price is SAR 1,122
SAR 1,294 total
includes taxes & fees
16 Nov - 17 Nov
Glen Gordon Manor
A traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.

2. Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
9.2 out of 10, Wonderful, (693 reviews)
"It was beautiful location. The staff was amazing and the food was excellent highly recommend."
United States
Cecile
The price is SAR 559
SAR 720 total
includes taxes & fees
22 Nov - 23 Nov
Hillbrook Inn
A gazebo with a brick pathway leading to it, surrounded by a grassy area with purple flowers.

3. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (340 reviews)
"Very nice with adjacent winery!"
United States
Julia
The price is SAR 552
SAR 629 total
includes taxes & fees
10 Dec - 11 Dec
Loudoun Valley Manor
A staircase with a stone wall, wooden steps, and a red carpet leading to a room with a wooden table and chairs.

4. Light Horse Inn

Light Horse Inn
2.0 star property
Harpers Ferry
9.4 out of 10, Exceptional, (161 reviews)
"Great place and breakfast was amazing!!"
United States
Rich
The price is SAR 491
SAR 525 total
includes taxes & fees
18 Nov - 19 Nov
Light Horse Inn
A rural property with a barn, a white house, and a white fence.

5. Stable & Vine

Stable & Vine
3.5 star property
Leesburg
10.0 out of 10, Exceptional, (7 reviews)
"Really nice property, very clean very quiet. off the beaten path, perfect for us"
United States
david
The price is SAR 860
SAR 980 total
includes taxes & fees
15 Nov - 16 Nov
Stable & Vine
A hallway with a dark wooden floor, white walls, and a large mirror on the right. There is a door at the end of the hallway and a small table with a vase of flowers on the left.

6. Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.6 out of 10, Exceptional, (147 reviews)
"I loved the charm of the inn, and I had my best sleep of the week on their comfortable beds. The breakfast the next morning was delicious!! A great value for a bed and breakfast!!"
United States
Gary
The price is SAR 938
SAR 1,070 total
includes taxes & fees
10 Dec - 11 Dec
Inn at Evergreen
A two-story house with a porch and a small garden area.

7. Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
Sperryville
9.8 out of 10, Exceptional, (39 reviews)
"Staff was wonderful and caring! Breakfast was delicious. The tavern had wonderful beer and we enjoyed meeting Norman the beagle."
United States
Deborah
The price is SAR 935
SAR 1,078 total
includes taxes & fees
16 Nov - 17 Nov
Hopkins Ordinary Bed Breakfast and Ale Works
A cozy seating area with two rocking chairs and a small table, overlooking a lush garden through a large arched window.

8. Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (37 reviews)
"Drew and the team were fantastic. It’s such a cute little inn. Very comfortable."
Canada
Dalton
The price is SAR 1,274
SAR 1,374 total
includes taxes & fees
10 Dec - 11 Dec
Gay Street Inn
A grand staircase with a chandelier, leading to an open doorway with a view of a garden.

9. The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.2 out of 10, Wonderful, (10 reviews)
"Beautiful venue, great service, and very close to the local downtown. Would stay again, highly recommend. "
United States
Robert
The price is SAR 2,189
SAR 2,495 total
includes taxes & fees
10 Nov - 11 Nov
The Inn at Grass Roots Hill
A large two-story house with a stone exterior, a covered porch, and a well-maintained garden.

10. Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Lovettsville
10.0 out of 10, Exceptional, (1 review)
"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 SAR 43,169
SAR 55,564 total
includes taxes & fees
11 Nov - 12 Nov
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

11. Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
10.0 out of 10, Exceptional, (2 reviews)
"We only spent one night here because my wife had training in the town of Purcellville. However, we were treated like family. Kenny, the general manager, was very kind, welcoming and attentive. He personally prepared our breakfast. Noé, the caretaker was wonderful and always available to us. Beyond that, this is one of the most beautiful, scenic properties I have ever experienced. You have to see it for yourself. Highly recommended!"
United States
Andrew
The price is SAR 1,051
SAR 1,292 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A two-story house with a front porch, American flags, and a mailbox.

12. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.8 out of 10, Exceptional, (467 reviews)
"Beautiful place. Cookies were nice in the evenings and breakfast was delicious."
United States
Meredith
The price is SAR 632
SAR 715 total
includes taxes & fees
10 Nov - 11 Nov
The Carriage Inn B&B
A swimming pool with a white pergola and red flowers in the foreground, surrounded by green trees and a clear blue sky.

13. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (74 reviews)
"Perfect idyllic retreat -- lovely property, cozy room, AMAZING art and chill vibes. Lovely host, too. Would love to go back :)"
United States
Anonymous traveler
The price is SAR 1,314
SAR 1,553 total
includes taxes & fees
10 Nov - 11 Nov
The Van Gogh Room in Villa
A two-story house with a front porch, a central staircase, and a small tower-like structure on the roof.

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

Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (3 reviews)
"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 SAR 730
SAR 1,013 total
includes taxes & fees
15 Nov - 16 Nov
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
A backyard with a wooden deck, a pool, and a white fence.

15. Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Purcellville
9.8 out of 10, Exceptional, (40 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is SAR 1,502
SAR 1,969 total
includes taxes & fees
10 Nov - 11 Nov
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
A two-story house with a porch, a flag in front, and a white picket fence.

16. The Botany at Blue Ridge Botanica

The Botany at Blue Ridge Botanica
Luray
The Botany at Blue Ridge Botanica
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

17. Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
10.0 out of 10, Exceptional, (1 review)
"The location was perfect since there aren’t many B&B places or hotels in Purceville. It’s a beautiful area and a beautiful venue."
United States
Kathleen
The price is SAR 1,182
SAR 1,451 total
includes taxes & fees
15 Nov - 16 Nov
Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A two-story house with a front porch, a central staircase, and a small tower-like structure on the roof.

18. 50's Drive-In Inside the Grand Castalian Inn B&B

50's Drive-In Inside the Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (1 review)
The price is SAR 816
SAR 1,115 total
includes taxes & fees
12 Nov - 13 Nov
50's Drive-In Inside the Grand Castalian Inn B&B
A two-story house with a front porch, a central staircase, and a small tower-like structure on the roof.

19. Appalachian Suite In Town!- The Grand Castalian Inn B&B

Appalachian Suite In Town!- The Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
"We loved the spot and will be back!"
United States
Seth W.
The price is SAR 773
SAR 1,066 total
includes taxes & fees
12 Nov - 13 Nov
Appalachian Suite In Town!- The Grand Castalian Inn B&B
A two-story house with a porch, a flag in front, and a white picket fence.

20. The Aviary at Blue Ridge Botanica

The Aviary at Blue Ridge Botanica
Luray
The price is SAR 1,032
SAR 1,281 total
includes taxes & fees
24 Nov - 25 Nov
The Aviary at Blue Ridge Botanica
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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Winchester and related destinations

Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theater.

See all hotels in Winchester
A white neoclassical building with columns, an American flag, and a clock tower.

Top reviews in Winchester

A traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.
Hillbrook Inn

Hillbrook Inn

Hillbrook Inn
Charles Town

10/10 Excellent

This is an Inn in a very rural area. It is very peaceful and this was much needed to quiet the mind. I went on the verge of the leaves changing in the fall so it was quite beautiful with changing leaves but still green grass and some plants blooming. I brought my small dog in this solo trip and it was a nice touch to leave a couple of milk bones in the room for him. I didn't go to the dining area for breakfast or dinner so I can't comment of this portion.
United States
Patti
Reviewed October 17, 2023
Hillbrook Inn

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: Hillbrook Inn: 9 rooms. 13.5 mi (21.7 km) from the downtown core. Enjoy the free full breakfast and fitness center. The Carriage Inn B&B: 7 rooms. 18.2 mi (29.3 km) from the heart of downtown. Enjoy the designer toiletries and in-room fireplace.

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.