Winchester B&B: Find the Best Bed and Breakfast from CA $212

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Winchester bed & breakfast

1. Glen Gordon Manor

Huntly

Alexander and Judith

CA $515 total

includes taxes & fees

Aug 4 - Aug 5

2. Hillbrook Inn

Charles Town

Cecile

CA $248 total

includes taxes & fees

Aug 13 - Aug 14

3. Loudoun Valley Manor

Waterford

michael

CA $233 total

includes taxes & fees

Aug 4 - Aug 5

4. Stone Manor Boutique Inn

Lovettsville

Linda

CA $372 total

includes taxes & fees

Aug 2 - Aug 3

5. The Inn at Grass Roots Hill

Purcellville

Robert

CA $659 total

includes taxes & fees

Aug 1 - Aug 2

6. Light Horse Inn

Harpers Ferry

David

CA $218 total

includes taxes & fees

Aug 4 - Aug 5

7. Cantuta Inn

Harpers Ferry

Anthony

CA $212 total

includes taxes & fees

Aug 2 - Aug 3

8. Inn at Evergreen

Haymarket

Kristine

CA $411 total

includes taxes & fees

Aug 2 - Aug 3

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

Purcellville

Dennis G.

CA $685 total

includes taxes & fees

Aug 3 - Aug 4

10. Light Horse Inn: Suite 6

Bolivar

Theresa

CA $313 total

includes taxes & fees

Aug 11 - Aug 12

11. The Van Gogh Room in Villa

Purcellville

Tom W.

CA $583 total

includes taxes & fees

Aug 2 - Aug 3

12. The Carriage Inn B&B

Charles Town

Andrea

CA $240 total

includes taxes & fees

Aug 3 - Aug 4

13. 50's Drive-In Inside the Grand Castalian Inn B&B

Berkeley Springs

CA $479 total

includes taxes & fees

Aug 2 - Aug 3

14. Light Horse Inn: Suite 3

Harpers Ferry

CA $340 total

includes taxes & fees

Aug 11 - Aug 12

15. Light Horse Inn: Suite 4

Harpers Ferry

Caryl R.

CA $330 total

includes taxes & fees

Aug 11 - Aug 12

16. Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included

Purcellville

CA $699 total

includes taxes & fees

Aug 11 - Aug 12

17. Hopkins Ordinary Bed Breakfast and Ale Works

Sperryville

Deborah

CA $363 total

includes taxes & fees

Aug 11 - Aug 12

18. Gay Street Inn

Washington

Renee

CA $483 total

includes taxes & fees

Aug 13 - Aug 14

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

Berkeley Springs

Deirdre A.

CA $476 total

includes taxes & fees

Aug 1 - Aug 2

20. Light Horse Inn: Suite 7

Bolivar

Rebecca

CA $313 total

includes taxes & fees

Aug 6 - Aug 7

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Comfort Inn & Suites Winchester

10/10 Excellent

"Very clean hotel with friendly desk staff. We always stay here on our trips north-south and it’s super comfortable."

Mimslyn Inn Historic Hotels Of America

10/10 Excellent

"We enjoyed our stay at the Mimslyn Inn and would gladly stay there again. The inn was clean, the grounds were beautiful, and every staff member we encountered was friendly, helpful, and welcoming. We chose the Mimslyn for two main reasons: its historic character and its convenient location. It was less than a five-minute drive from Luray Caverns, which was the main reason for our trip, and it was also close to downtown Luray. Guests should keep in mind that this is a historic inn, so the experience is a little different from staying in a modern hotel. Our room did not have a mini-fridge, microwave, or coffee maker. However, a shared refrigerator and microwave were available for guests, and complimentary coffee was provided in the mornings. The room also had what I would describe as a noticeable “historic” smell. We did not consider it a bad thing—it was part of the character and charm of an older building—but guests who are accustomed to newer hotels may want to be aware of it. The inn is technically within walking distance of downtown, but the hills make it more of a hike than a casual stroll. Driving may be preferable for guests who have mobility concerns or simply want a more relaxing trip into town. Overall, the Mimslyn Inn is a beautiful, historic property with excellent service and a convenient location. We appreciated its character and would stay there again."

Spark by Hilton Winchester

10/10 Excellent

"J'ai noté cet hôtel 5 étoiles ce qui est très bien. La chambre et la salle de bain étaient très propre. Il y avait suffisamment de serviettes pour la douche. La personne à l'accueil etait courtoise mais souvent retranchée derrière le mur. Le Hall d'entrée est très grand et bien aménagé avec beaucoup de fauteuils pour relaxer. Le petit déjeuner inclus était bien sans plus. La salle à manger était propre avec suffisamment de de tables et chaises. Bon restaurant très près de l'hôtel. Stationnement sécuritaire. J'ai vraiment apprécié mon séjour.."

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent

"This site is fairly close to the Interstate and convenient for travelers. As expected, the Holiday Inn lived up to our expectations. The room was clean and comfortable. The staff was friendly. The breakfast was good and adequate. I would definitely stay here again should travel take me this way."

Find out more about Winchester

Winchester B&B information

Number of reviews	1,410
Accommodation	48 B&B
Lowest Price	CA $212
Highest Price	CA $699

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 $212 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.

Explore a world of travel with Expedia

Book B&B in Winchester on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester bed & breakfast

1. Glen Gordon Manor

2. Hillbrook Inn

3. Loudoun Valley Manor

4. Stone Manor Boutique Inn

5. The Inn at Grass Roots Hill

6. Light Horse Inn

7. Cantuta Inn

8. Inn at Evergreen

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

10. Light Horse Inn: Suite 6

11. The Van Gogh Room in Villa

12. The Carriage Inn B&B

13. 50's Drive-In Inside the Grand Castalian Inn B&B

14. Light Horse Inn: Suite 3

15. Light Horse Inn: Suite 4

16. Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included

17. Hopkins Ordinary Bed Breakfast and Ale Works

18. Gay Street Inn

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

20. Light Horse Inn: Suite 7

Top Winchester Hotel Reviews

Comfort Inn & Suites Winchester

La Quinta Inn & Suites by Wyndham Winchester

Mimslyn Inn Historic Hotels Of America

Hilton Garden Inn Dulles North

Quality Inn Winchester

Spark by Hilton Winchester

Holiday Inn Winchester Se-Historic Gateway by IHG

Fairfield Inn & Suites by Marriott Winchester

Country Inn & Suites by Radisson, Winchester, VA

Find out more about Winchester

Winchester B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find a Bed and Breakfast in Winchester from CA $212

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester bed & breakfast

1. Glen Gordon Manor

2. Hillbrook Inn

3. Loudoun Valley Manor

4. Stone Manor Boutique Inn

5. The Inn at Grass Roots Hill

6. Light Horse Inn

7. Cantuta Inn

8. Inn at Evergreen

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

10. Light Horse Inn: Suite 6

11. The Van Gogh Room in Villa

12. The Carriage Inn B&B

13. 50's Drive-In Inside the Grand Castalian Inn B&B

14. Light Horse Inn: Suite 3

15. Light Horse Inn: Suite 4

16. Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included

17. Hopkins Ordinary Bed Breakfast and Ale Works

18. Gay Street Inn

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

20. Light Horse Inn: Suite 7

Top Winchester Hotel Reviews

Comfort Inn & Suites Winchester

Find out more about Winchester

Winchester B&B information

Frequently asked questions

Explore a world of travel with Expedia