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B&B in Winchester

Front of property
Homestay BnB Near Downtown Boston

Homestay BnB Near Downtown Boston

2.0 star property
Dorchester
8.6 out of 10, Excellent, (141)
"Thank you perfect place to stay "
United States
Iuliia
Homestay BnB Near Downtown Boston
Standard Double Room | Interior
Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston

2.0 star property
Dorchester
10.0 out of 10, Exceptional, (1)
"Great house!"
United States
Liang
$49 nightly
The price is $56
Dec 7 - Dec 8
Total with taxes and fees
Homestay In Fields Corner Area Boston
Miscellaneous
The College Club of Boston

The College Club of Boston

3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1000)
"Everything! Tbh my fave was the cookies! It was the perfect stay in the heart of it all while being super quiet for a solo traveler! "
United States
Haley
$179 nightly
The price is $206
Jan 1 - Jan 2, 2026
Total with taxes and fees
The College Club of Boston
Property grounds
The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston

Brighton
9.6 out of 10, Exceptional, (60)
"Great location and wonderful host"
United States
Robert M.
$150 nightly
The price is $172
Dec 3 - Dec 4
Total with taxes and fees
The Pistachio Room at TPH - Boston
Exterior detail
Irving House At Harvard

Irving House At Harvard

3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1006)
"nice but very small room, staff very good"
United States
Francesco
$135 nightly
The price is $155
Dec 17 - Dec 18
Total with taxes and fees
Irving House At Harvard
Exterior
Homestay Near Downtown Boston

Homestay Near Downtown Boston

2.0 star property
Dorchester
$77 nightly
The price is $89
Dec 3 - Dec 4
Total with taxes and fees
Homestay Near Downtown Boston
King Luxury Suite Overlooking the Bay | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Beacon Waterfront Inn

The Beacon Waterfront Inn

3.0 star property
Hull
9.4 out of 10, Exceptional, (301)
"Beautiful spacious room "
United States
Maryann
$149 nightly
The price is $163
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Beacon Waterfront Inn
Front of property
The Salem Inn

The Salem Inn

3.5 star property
Salem
9.2 out of 10, Wonderful, (1000)
"Very clean and lovely atmosphere! Definitely grateful to stay here so I could walk everywhere! All the cool places are in walking distance."
United States
Chelsey
$180 nightly
The price is $201
Dec 3 - Dec 4
Total with taxes and fees
The Salem Inn
Classic Triple Room | Interior
Homestay In Boston -

Homestay In Boston -

2.0 star property
Dorchester
$62 nightly
The price is $72
Dec 3 - Dec 4
Total with taxes and fees
Homestay In Boston -
Front of property
Daniels House Inn

Daniels House Inn

3.0 star property
Salem
9.4 out of 10, Exceptional, (100)
"This property is amazing. The home and rooms are clean, comfortable and beautiful. "
United States
Rachel
$274 nightly
The price is $274
Dec 3 - Dec 4
Total with taxes and fees
Daniels House Inn
Private kitchen
Charming B&B close to Salem and Boston

Charming B&B close to Salem and Boston

2.0 star property
Lynn
5.8 out of 10, (16)
"Very quiet at night was great for resting. Great place to visit and stay. "
United States
Orlando M.
Charming B&B close to Salem and Boston
Front of property
North Bridge 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
Dec 3 - Dec 4
Total with taxes and fees
North Bridge Inn
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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Staff was very friendly and helpful. Rooms were clean and new. "
Rosemarie 3-night trip
Posted 1 day ago
Omni Boston Hotel at the Seaport

Find out more about Winchester

Winchester B&B information

Number of reviews
3,663
Accommodation
28 B&B
Lowest Price
$155
Highest Price
$274

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 $155 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.

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