A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Check prices for these dates

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov
In one month
27 Nov - 29 Nov
In two months
25 Dec - 27 Dec

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
9.8 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 HK$2,189
HK$2,524 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 HK$1,169
HK$1,505 total
includes taxes & fees
3 Nov - 4 Nov
Hillbrook Inn
A spacious living room with a wooden floor, a large sofa, a coffee table, and a dining area with a wooden table and chairs.

3. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (335 reviews)
"Very nice with adjacent winery!"
United States
Julia
The price is HK$1,177
HK$1,341 total
includes taxes & fees
1 Nov - 2 Nov
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, (158 reviews)
"Great place and breakfast was amazing!!"
United States
Rich
The price is HK$1,165
HK$1,247 total
includes taxes & fees
8 Nov - 9 Nov
Light Horse Inn
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.

5. 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 HK$2,030
HK$2,314 total
includes taxes & fees
1 Nov - 2 Nov
Inn at Evergreen
A rural property with a barn, a white house, and a white fence.

6. 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 HK$2,066
HK$2,355 total
includes taxes & fees
1 Nov - 2 Nov
Stable & Vine
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 HK$2,025
HK$2,335 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 HK$2,535
HK$2,732 total
includes taxes & fees
19 Nov - 20 Nov
Gay Street Inn
A large two-story house with a stone exterior, a covered porch, and a well-maintained garden.

9. 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 HK$90,213
HK$121,957 total
includes taxes & fees
4 Nov - 5 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.

10. 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 HK$2,196
HK$2,826 total
includes taxes & fees
4 Nov - 5 Nov
Cozy Lakefront 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.

11. 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 HK$1,705
HK$2,431 total
includes taxes & fees
2 Nov - 3 Nov
50's Drive-In Inside the Grand Castalian Inn B&B
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
9.6 out of 10, Exceptional, (467 reviews)
"Beautiful place. Cookies were nice in the evenings and breakfast was delicious."
United States
Meredith
The price is HK$1,322
HK$1,493 total
includes taxes & fees
5 Nov - 6 Nov
The Carriage Inn B&B
A grand staircase with a chandelier, leading to an open doorway with a view of a garden.

13. 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 HK$4,574
HK$5,214 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Grass Roots Hill
A two-story house with a porch, a flag in front, and a white picket fence.

14. The Botany at Blue Ridge Botanica

The Botany at Blue Ridge Botanica
Luray
The price is HK$2,157
HK$2,849 total
includes taxes & fees
10 Nov - 11 Nov
The Botany at Blue Ridge Botanica
A swimming pool with a white pergola and red flowers in the foreground, surrounded by green trees and a clear blue sky.

15. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (73 reviews)
"Perfect idyllic retreat -- lovely property, cozy room, AMAZING art and chill vibes. Lovely host, too. Would love to go back :)"
United States
Anonymous traveller
The price is HK$2,746
HK$3,559 total
includes taxes & fees
1 Nov - 2 Nov
The Van Gogh Room in Villa
A backyard with a wooden deck, a pool, and a white fence.

16. 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, (39 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is HK$3,138
HK$4,319 total
includes taxes & fees
1 Nov - 2 Nov
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
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 HK$2,471
HK$3,175 total
includes taxes & fees
4 Nov - 5 Nov
Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A hallway with a wooden staircase, a chandelier, a brick fireplace, and a patterned rug.

18. 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 HK$1,525
HK$2,202 total
includes taxes & fees
2 Nov - 3 Nov
Bird Nest Suite In Town!- 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 HK$1,615
HK$2,320 total
includes taxes & fees
12 Nov - 13 Nov
Appalachian Suite In Town!- 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.

20. River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B

River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (4 reviews)
"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 HK$1,615
HK$2,320 total
includes taxes & fees
2 Nov - 3 Nov
River Retreat Suite In Town!- 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

Skyland

Skyland

8/10 Good
"The shower had rather low water pressure and it took a couple tries to get the space heater in the bathroom to work. Other than that, clean comfortable room."
Robert 3-night trip
Posted 4 hours ago
Skyland

Find out more about Winchester

Winchester B&B information

Number of reviews
1,825
Accommodation
47 B&B
Lowest Price
HK$1,247
Highest Price
HK$121,957

Frequently asked questions

Searching for B&Bs in Winchester?
Whether you're on a romantic holiday and want to stay somewhere quiet, or you're travelling solo and looking to chat with locals, B&Bs can be a great choice for many travellers. If your ideal holiday 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 a unique charm — whether it's a cosy reading space or a sunlit breakfast nook, the quaint details are what make bed and breakfasts the perfect escape.
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 city centre. Enjoy the free full breakfast and fitness centre. The Carriage Inn B&B: 7 rooms. 18.2 mi (29.3 km) from the city centre. Enjoy the designer toiletries and in-room fireplace.
What's the best time of year to stay at a B&B in Winchester?
When you're planning your getaway to Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
What is there to do in Winchester?
Travellers who want to experience Winchester should visit 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 should 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?
Planning your excursions in and around Winchester is easier 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. Otherwise, you can search for flights to Washington Dulles International Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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