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

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 CA $376
CA $433 total
includes taxes & fees
Nov 4 - Nov 5
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 CA $208
CA $268 total
includes taxes & fees
Nov 3 - Nov 4
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, (336 reviews)
"Very nice with adjacent winery!"
United States
Julia
The price is CA $197
CA $225 total
includes taxes & fees
Dec 1 - Dec 2
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, (160 reviews)
"Great place and breakfast was amazing!!"
United States
Rich
The price is CA $176
CA $189 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $362
CA $412 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $313
CA $357 total
includes taxes & fees
Dec 1 - Dec 2
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 CA $361
CA $416 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $441
CA $476 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $16,070
CA $20,148 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $391
CA $481 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $304
CA $418 total
includes taxes & fees
Nov 8 - Nov 9
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
9.8 out of 10, Exceptional, (467 reviews)
"Beautiful place. Cookies were nice in the evenings and breakfast was delicious."
United States
Meredith
The price is CA $235
CA $266 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $815
CA $929 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $384
CA $482 total
includes taxes & fees
Nov 4 - Nov 5
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 CA $489
CA $604 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $559
CA $733 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $440
CA $542 total
includes taxes & fees
Nov 7 - Nov 8
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. 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 CA $272
CA $379 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $288
CA $398 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $288
CA $398 total
includes taxes & fees
Nov 2 - Nov 3
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"This a very nice place to stay. The breakfast hit the spot. We would stay here again."
Betsy 1-night trip
Posted 11 hours ago
TRU By Hilton Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
1,828
Accommodation
44 B&B
Lowest Price
CA $189
Highest Price
CA $20,148

Frequently asked questions

What is the nightly rate for a B&B in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from CA $189 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Winchester?
The best time to book a B&B in Winchester is during the vibrant spring months of March to May. This period sees the city come alive with blooming flowers and outdoor events, making it a splendid time for travellers looking to enjoy the rich history and scenic beauty of the area. With pleasant temperatures averaging in the mid-teens Celsius, exploring Winchester's historic sites, such as the iconic Winchester Cathedral and the Great Hall, becomes a delightful experience.

April, in particular, is a popular choice for visitors, as it offers a wonderful blend of comfortable weather and lively local festivals, such as the Winchester Science Festival. The mild climate encourages outdoor strolls through the picturesque gardens and along the River Itchen, superb for those who appreciate a blend of culture and nature.

For those seeking a more budget-friendly option, consider visiting in November. This month allows for a quieter experience, where you can enjoy the charm of Winchester's historic streets adorned for the festive season. It's an ideal time for leisurely exploration, with the city's attractions less crowded and often offering special events and markets.
What is the difference between a Winchester B&B and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

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