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

Find a Bed and Breakfast in Winchester from CA $221

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Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15

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, (98 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
The price is CA $471
CA $543 total
includes taxes & fees
Sep 21 - Sep 22
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
8.6 out of 10, Excellent, (691 reviews)
"It was beautiful location. The staff was amazing and the food was excellent highly recommend."
United States
Cecile
The price is CA $188
CA $246 total
includes taxes & fees
Oct 1 - Oct 2
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, (331 reviews)
"This facility was excellent in every area. Thanks for great custom breakfast omlets."
United States
Michael
The price is CA $208
CA $238 total
includes taxes & fees
Sep 20 - Sep 21
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, (144 reviews)
"This is a very nice and relaxing inn with very helpful staff"
United States
David
The price is CA $207
CA $221 total
includes taxes & fees
Oct 6 - Oct 7
Light Horse Inn
An outdoor patio area with tables and chairs, umbrellas, barrels, and a wooden building.

5. Stable & Vine

Stable & Vine
3.5 star property
Leesburg
The price is CA $302
CA $345 total
includes taxes & fees
Sep 23 - Sep 24
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
9.4 out of 10, Exceptional, (140 reviews)
"A very beautiful experience. The staff was amazing. The country club access was such a treat. The room was breathtaking. We can’t wait to go back:"
United States
Adriane
The price is CA $358
CA $408 total
includes taxes & fees
Sep 24 - Sep 25
Inn at Evergreen
A two-story house with a front porch, a central staircase, and a small tower-like structure on the roof.

7. 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 $302
CA $437 total
includes taxes & fees
Sep 23 - Sep 24
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Two people seated at a table with a view of a sunset over a hilly landscape.

8. 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 $556
CA $770 total
includes taxes & fees
Sep 21 - Sep 22
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Two people seated at a table with a view of a sunset over a hilly landscape.

9. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (71 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 $452
CA $583 total
includes taxes & fees
Sep 18 - Sep 19
The Van Gogh Room in Villa
A cozy seating area with two rocking chairs and a small table, overlooking a lush garden through a large arched window.

10. Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (36 reviews)
"Super cute place! Drew was so helpful and friendly. Loved the breakfast and the whole vibe of the house. Highly recommend,"
United States
Kathryn
The price is CA $449
CA $484 total
includes taxes & fees
Sep 24 - Sep 25
Gay Street Inn
A grand staircase with a chandelier, leading to an open doorway with a view of a garden.

11. 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 $810
CA $924 total
includes taxes & fees
Sep 20 - Sep 21
The Inn at Grass Roots Hill
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, (455 reviews)
"Amazing place with incredible history!"
United States
Andrea
The price is CA $213
CA $241 total
includes taxes & fees
Sep 17 - Sep 18
The Carriage Inn B&B
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

13. 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
The price is CA $438
CA $566 total
includes taxes & fees
Sep 22 - Sep 23
Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A two-story house with a porch and a small garden area.

14. 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, (38 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 $386
CA $445 total
includes taxes & fees
Sep 22 - Sep 23
Hopkins Ordinary Bed Breakfast and Ale Works
A large two-story house with a stone exterior, a covered porch, and a well-maintained garden.

15. 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 $15,983
CA $20,791 total
includes taxes & fees
Sep 20 - Sep 21
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
A two-story house with a front porch, a central staircase, and a small tower-like structure on the roof.

16. 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 $318
CA $453 total
includes taxes & fees
Sep 23 - Sep 24
River Retreat 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.

17. 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 $318
CA $453 total
includes taxes & fees
Sep 23 - Sep 24
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.

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 CA $334
CA $476 total
includes taxes & fees
Sep 17 - Sep 18
50's Drive-In Inside the Grand Castalian Inn B&B
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

19. 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 $389
CA $502 total
includes taxes & fees
Sep 22 - Sep 23
Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

20. Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included

Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
The price is CA $486
CA $629 total
includes taxes & fees
Sep 22 - Sep 23
Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
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

10/10 Excellent
"The rooms were very comfortable and clean. Area around was safe. Staff was very helpful and welcoming."
Larry 2-night trip
Posted 5 hours ago
Skyland

Find out more about Winchester

Winchester B&B information

Number of reviews
744
Accommodation
48 B&B
Lowest Price
CA $221
Highest Price
CA $20,791

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 $221 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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