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Our top choices for Winchester bed & breakfast

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 £256
includes taxes & fees
16 Nov - 17 Nov
Glen Gordon Manor

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 £143
includes taxes & fees
9 Nov - 10 Nov
Hillbrook Inn

3. 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 £104
includes taxes & fees
18 Nov - 19 Nov
Light Horse Inn

4. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (339 reviews)
"Very nice with adjacent winery!"
United States
Julia
The price is £122
includes taxes & fees
6 Dec - 7 Dec
Loudoun Valley Manor

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 £219
includes taxes & fees
3 Dec - 4 Dec
Inn at Evergreen

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 £187
includes taxes & fees
6 Dec - 7 Dec
Stable & Vine

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 £214
includes taxes & fees
17 Nov - 18 Nov
Hopkins Ordinary Bed Breakfast and Ale Works

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 £282
includes taxes & fees
12 Nov - 13 Nov
Gay Street Inn

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 £10,954
includes taxes & fees
16 Nov - 17 Nov
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

10. 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 £493
includes taxes & fees
8 Nov - 9 Nov
The Inn at Grass Roots Hill

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 £259
includes taxes & fees
16 Nov - 17 Nov
Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

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 £141
includes taxes & fees
19 Nov - 20 Nov
The Carriage Inn B&B

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 traveller
The price is £323
includes taxes & fees
8 Nov - 9 Nov
The Van Gogh Room in Villa

14. 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 £223
includes taxes & fees
8 Nov - 9 Nov
50's Drive-In Inside the Grand Castalian Inn B&B

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 £384
includes taxes & fees
8 Nov - 9 Nov
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

16. Mayneview B&B

Mayneview B&B
4.0 star property
Luray
8.6 out of 10, Excellent, (419 reviews)
"The decorations and location is fantastic"
United States
Nurit Norma
The price is £267
includes taxes & fees
7 Nov - 8 Nov
Mayneview B&B

17. The Botany at Blue Ridge Botanica

The Botany at Blue Ridge Botanica
Luray
The price is £257
includes taxes & fees
8 Nov - 9 Nov
The Botany at Blue Ridge Botanica

18. 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 £287
includes taxes & fees
16 Nov - 17 Nov
Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

19. 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 £202
includes taxes & fees
9 Nov - 10 Nov
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B

20. 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 £212
includes taxes & fees
12 Nov - 13 Nov
Appalachian Suite In Town!- 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.

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 Theatre.

A white neoclassical building with columns, an American flag, and a clock tower.

Top reviews in Winchester

Frequently Asked Questions

What is the nightly rate for a Bed & Breakfast in Winchester?

Prices for B&Bs in Winchester often vary, but you can find a great deal from £104 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 Bed and Breakfast 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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