Book Winchester Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out
  • 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
In two weeks
In one month
In two months

B&B in Winchester

Homestay BnB Near Downtown Boston

2.0 star property
Dorchester
8.6 out of 10, Excellent, (122)
"Thank you perfect place to stay "
United States
Iuliia
$87 nightly
The price is $101
Nov 11 - Nov 12
Total with taxes and fees
Homestay BnB Near Downtown Boston

The Pistachio Room at TPH - Boston

Brighton
9.6 out of 10, Exceptional, (57)
"Clean, safe, comfy, excellent communications from host!"
United States
Sue M.
$150 nightly
The price is $172
Nov 11 - Nov 12
Total with taxes and fees
The Pistachio Room at TPH - Boston

Irving House At Harvard

3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1001)
"Great location"
United States
Thomas
$145 nightly
The price is $166
Nov 23 - Nov 24
Total with taxes and fees
Irving House At Harvard

The College Club of Boston

3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1001)
"Great location. Perfect for my short stay for business. "
United States
Oscar
$259 nightly
The price is $298
Nov 16 - Nov 17
Total with taxes and fees
The College Club of Boston

The Beacon Waterfront Inn

3.0 star property
Hull
9.4 out of 10, Exceptional, (300)
"Staff was very friendly and very helpful with helping us where to go eat and how to get to Salem. "
United States
Jennifer
$169 nightly
The price is $185
Nov 11 - Nov 12
Total with taxes and fees
The Beacon Waterfront Inn

Château sur Mer Bed & Breakfast

3.0 star property
Winthrop
8.6 out of 10, Excellent, (211)
"Nice place to stay "
United States
Sam
$189 nightly
The price is $211
Nov 11 - Nov 12
Total with taxes and fees
Château sur Mer Bed & Breakfast

The Salem Inn

3.5 star property
Salem
9.2 out of 10, Wonderful, (1002)
"Great location and comfortable!"
United States
Teresa
$180 nightly
The price is $201
Nov 12 - Nov 13
Total with taxes and fees
The Salem Inn

Daniels House Inn

3.0 star property
Salem
9.4 out of 10, Exceptional, (99)
"Absolutely one of a kind historic home - it ended up being the very best part of our trip. The housekeeper was lovely, the breakfast and decor are thoughtful and elegant."
United States
Elizabeth
$255 nightly
The price is $255
Dec 2 - Dec 3
Total with taxes and fees
Daniels House Inn

North Bridge Inn

3.5 star property
Concord
8.4 out of 10, Very Good, (349)
"Hot breakfast, attentive staff, proximity to a lot of history including Boston"
United States
Martin
$195 nightly
The price is $218
Nov 30 - Dec 1
Total with taxes and fees
North Bridge Inn

Charming B&B close to Salem and Boston

2.0 star property
Lynn
5.6 out of 10, (14)
"Inexpensive and close to many attractions. "
United States
Maria
$194 nightly
The price is $213
Nov 11 - Nov 12
Total with taxes and fees
Charming B&B close to Salem and Boston
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Find out more about Winchester

Winchester B&B information

Number of reviews
3,842
Accommodation
28 B&B
Lowest Price
$101
Highest Price
$298

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $101 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 peak season from April to June. This vibrant period attracts travelers eager to explore the charming historic sites and enjoy the blooming landscapes of the Shenandoah Valley. Visitors can immerse themselves in the rich heritage of the area while partaking in outdoor activities, such as hiking along scenic trails or leisurely strolls through picturesque gardens.

April, in particular, is a fantastic month to visit. The temperatures typically range from the mid-40s to mid-70s Fahrenheit, creating a comfortable climate for sightseeing and outdoor adventures. You'll find the local flora in full bloom, enhancing the beauty of Winchester's famous landmarks, including the stunning Handley Regional Library and the historic Old Town.

If you're looking for a more budget-friendly time to visit, consider planning your trip in November. This month offers a quieter experience, allowing for intimate exploration of the town's attractions without the usual crowds. The autumn foliage adds a unique charm to the surroundings, making it a great time for scenic drives and photography.
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