A calm lake with autumn foliage, a dock, and houses along the shore.

Book Winchester Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18

Our top choices for Winchester bed & breakfast

Interior

1. Nostalgic Q ensuite room in historic railroad inn.

Nostalgic Q ensuite room in historic railroad inn.
Cowan
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful spot!"
United States
Bennett R.
$186 nightly
The price is $213
Sep 1 - Sep 2
Total with taxes and fees
Nostalgic Q ensuite room in historic railroad inn.
Lobby

2. Artsy pet-friendly Q room in historic railroad inn

Artsy pet-friendly Q room in historic railroad inn
Cowan
9.4 out of 10, Exceptional, (6 reviews)
"Nice, clean room. Had everything we needed. Rachel was very helpful and friendly!"
United States
Brenda L.
$211 nightly
The price is $241
Aug 21 - Aug 22
Total with taxes and fees
Artsy pet-friendly Q room in historic railroad inn
Exterior

3. Tolley House

Tolley House
3.0 star property
Lynchburg
9.6 out of 10, Exceptional, (45 reviews)
"Friendly hosts, wonderful location"
United Kingdom
charmain
$195 nightly
The price is $225
Aug 28 - Aug 29
Total with taxes and fees
Tolley House
Property grounds

4. Mulberry Lavender Farm and B&B

Mulberry Lavender Farm and B&B
3.0 star property
Mulberry
9.6 out of 10, Exceptional, (37 reviews)
"I loved interacting with all the animals. My room was cozy. The owners took good care of me and were very accommodating with my work schedule."
United States
Joseph Francis Kowalczyk
$219 nightly
The price is $243
Sep 7 - Sep 8
Total with taxes and fees
Mulberry Lavender Farm and B&B
Lobby

5. Cozy king ensuite room in historic railroad inn

Cozy king ensuite room in historic railroad inn
Cowan
9.4 out of 10, Exceptional, (13 reviews)
"The Inn is a delightful place to originate daily excursions in the area. We were there for an event at Sewanee and it is in an ideal location for access to the University and also the adjacent communities."
United States
Jeff
$211 nightly
The price is $241
Aug 21 - Aug 22
Total with taxes and fees
Cozy king ensuite room in historic railroad inn
Interior

6. Artsy pet-friendly king room/historic railroad inn

Artsy pet-friendly king room/historic railroad inn
Cowan
9.4 out of 10, Exceptional, (10 reviews)
"Pretty Inn with lots of character and charm."
United States
Jennifer C.
$222 nightly
The price is $255
Aug 21 - Aug 22
Total with taxes and fees
Artsy pet-friendly king room/historic railroad inn
Exterior

7. Room 3 Belmont Inn 1852 Historic Evans House King in room private Bath 2nd Floor

Room 3 Belmont Inn 1852 Historic Evans House King in room private Bath 2nd Floor
Shelbyville
9.8 out of 10, Exceptional, (32 reviews)
"We enjoyed the BNB. It was great to stay in a home that has historic value."
United States
Paul H.
Room 3 Belmont Inn 1852 Historic Evans House King in room private Bath 2nd Floor
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Reflection Bay-Dock, Hot Tub, Kayaks

Reflection Bay-Dock, Hot Tub, Kayaks

10/10 Excellent
"Great clean property. Easy access to the lake with a good dock. As advertised."
adam s. 4-night trip
Posted 2 days ago
Reflection Bay-Dock, Hot Tub, Kayaks

Find out more about Winchester

Winchester B&B information

Number of reviews
82
Accommodation
5 B&B
Lowest Price
$225
Highest Price
$243

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 $225 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 most popular time to book a B&B in Winchester is during the peak season from May to July, when the area comes alive with vibrant activities and scenic beauty. This period attracts travelers seeking to enjoy the lush landscapes and warm weather, ideal for outdoor exploration and sightseeing. With temperatures ranging from the mid-50s to the low 80s Fahrenheit, visitors can comfortably partake in various activities, such as hiking the picturesque trails or exploring local wineries.

Among these months, July stands out as the height of summer fun, offering a lively atmosphere filled with festivals, farmers' markets, and community events. It's a great time for those who appreciate a bustling environment and the chance to mingle with fellow visitors while soaking up the sun.

For travelers looking for a more budget-friendly experience, consider visiting in November. This month, while quieter, offers a unique charm as the fall foliage begins to fade, providing a peaceful backdrop for leisurely strolls through Winchester's historic downtown or along the scenic Shenandoah River.
What is the difference between a Winchester Bed and Breakfast 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