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Check prices for these dates

Next weekend
Feb 6 - Feb 8
In two weeks
Feb 13 - Feb 15
In one month
Feb 27 - Mar 1
In two months
Mar 27 - Mar 29

Our top choices for Winchester bed & breakfast

Classic Triple Room | Interior

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.8 out of 10, Excellent, (15 reviews)
"The property was very clean and well maintained with spacious showers and a tv in your room. There are fresh towels as well as a free continental breakfast. The location has many restaurants/convenient stores not far away as well. Definitely recommend "
United States
Tyler
$63 nightly
The price is $73
Jan 29 - Jan 30
Total with taxes and fees
Homestay In Boston -
Full-size fridge, microwave, oven, stovetop

Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
8.8 out of 10, Excellent, (19 reviews)
"The entire place looks really amazing!"
United States
Jeremiah
$64 nightly
The price is $74
Jan 29 - Jan 30
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, (1,001 reviews)
"Outstanding location, pleasant facilities and staff, decent breakfast choices. "
United States
Mary
$169 nightly
The price is $194
Feb 1 - Feb 2
Total with taxes and fees
The College Club of Boston
Smart TV, fireplace

The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (61 reviews)
"Great location and wonderful host"
United States
Robert M.
$150 nightly
The price is $172
Jan 31 - Feb 1
Total with taxes and fees
The Pistachio Room at TPH - Boston
Interior

Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.0 out of 10, Very Good, (4 reviews)
"Very neat house "
United States
Nikhil
$61 nightly
The price is $71
Feb 28 - Mar 1
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, (305 reviews)
"The room was perfect, the house was perfect. The continental breakfast was poor. Oatmeal, Grits, pancakes, fresh fruit, banana "
United States
Chisulo
$149 nightly
The price is $166
Jan 29 - Jan 30
Total with taxes and fees
The Beacon Waterfront Inn
Exterior detail

Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,006 reviews)
"Staff still worked and fed us through a huge snow storm. Really appreciated that"
United States
Keoki
$125 nightly
The price is $143
Jan 29 - Jan 30
Total with taxes and fees
Irving House At Harvard
Front of property

Daniels House Inn

Daniels House Inn
3.0 star property
Salem
9.4 out of 10, Exceptional, (101 reviews)
"Clearly a well managed historic inn. Gorgeous, comfortable, unique, in a very walkable area. "
United States
April
$198 nightly
The price is $198
Feb 22 - Feb 23
Total with taxes and fees
Daniels House Inn
Exterior

The Salem Inn

The Salem Inn
3.5 star property
Salem
9.2 out of 10, Wonderful, (1,000 reviews)
"This place was great. We loved our stay."
United States
Jared
$180 nightly
The price is $201
Jan 29 - Jan 30
Total with taxes and fees
The Salem Inn
Front of property

North Bridge Inn

North Bridge Inn
3.5 star property
Concord
8.4 out of 10, Very Good, (349 reviews)
"Hot breakfast, attentive staff, proximity to a lot of history including Boston"
United States
Martin
$195 nightly
The price is $218
Jan 29 - Jan 30
Total with taxes and fees
North Bridge Inn
Basic Quadruple Room | Desk, laptop workspace, free WiFi

Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
2.0 out of 10, (1 review)
"The guy change the house and location at an interval I didn't have no option. He kept sending encrypted access code for the check in. He masked to send ID to he's WhatsApp. He doesn't reply on time. I told him parking spot is important for me while there wasn't none at the place he changed me to. For very long waiting I was having the the obligation to find another place. When I try to reach out to him he even don't read the message. I don't recommend this hoster. It was a bad experience and a...
United States
Jules Andre
$70 nightly
The price is $80
Jan 29 - Jan 30
Total with taxes and fees
Homestay Near Near Savin Hill Area
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

The Dagny Boston

The Dagny Boston

10/10 Excellent
"."
Tobey A Hanscom 2-night trip
Posted 1 day ago
The Dagny Boston

Find out more about Winchester

Winchester B&B information

Number of reviews
3,516
Accommodation
29 B&B
Lowest Price
$143
Highest Price
$218

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 $143 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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