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Check prices for these dates

Next weekend
13 Mar - 15 Mar
In two weeks
20 Mar - 22 Mar
In one month
3 Apr - 5 Apr
In two months
1 May - 3 May

Our top choices for Winchester bed & breakfast

Desk, laptop workspace, free WiFi

Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
8.4 out of 10, Very good, (25 reviews)
"The entire place looks really amazing!"
United States
Jeremiah
The price is AU$180
includes taxes & fees
8 Mar - 9 Mar
Homestay In Fields Corner Area Boston
Full-sized fridge, microwave, oven, stovetop

Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
9.2 out of 10, Wonderful, (15 reviews)
"Very clean, big rooms. Great breakfast options as well. For someone who just wants a home away from home, this is the place! "
United States
Zakir
The price is AU$202
includes taxes & fees
8 Mar - 9 Mar
Homestay Near Downtown Boston
Desk, laptop workspace, free WiFi

Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
7.4 out of 10, Good, (3 reviews)
"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
The price is AU$280
includes taxes & fees
19 Mar - 20 Mar
Homestay Near Near Savin Hill Area
Dining

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.4 out of 10, Very good, (20 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
The price is AU$245
includes taxes & fees
8 Mar - 9 Mar
Homestay In Boston -
Exterior

The Salem Inn

The Salem Inn
3.5 star property
Salem
9.2 out of 10, Wonderful, (1,001 reviews)
"This place was great. We loved our stay."
United States
Jared
The price is AU$284
includes taxes & fees
7 Mar - 8 Mar
The Salem Inn
King Luxury Suite Overlooking the Bay

The Beacon Waterfront Inn

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (306 reviews)
"The room was perfect, the house was perfect. The continental breakfast was poor. Oatmeal, Grits, pancakes, fresh fruit, banana "
United States
Chisulo
The price is AU$235
includes taxes & fees
16 Mar - 17 Mar
The Beacon Waterfront Inn
Exterior

Daniels House Inn

Daniels House Inn
3.0 star property
Salem
9.4 out of 10, Exceptional, (102 reviews)
"Clearly a well managed historic inn. Gorgeous, comfortable, unique, in a very walkable area. "
United States
April
The price is AU$278
includes taxes & fees
9 Mar - 10 Mar
Daniels House Inn
Miscellaneous

The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1,005 reviews)
"Outstanding location, pleasant facilities and staff, decent breakfast choices. "
United States
Mary
The College Club of Boston
Double Room, 1 Queen Bed

Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.6 out of 10, Excellent, (211 reviews)
"Very quaint and cute bed and breakfast with fun view of the bay and airplanes landing, cute restaurants nearby and super close to the airport. Great price for accommodations near Logan for early morning flight."
United States
Heidi
The price is AU$298
includes taxes & fees
1 Apr - 2 Apr
Château sur Mer Bed & Breakfast
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
The price is AU$308
includes taxes & fees
9 Mar - 10 Mar
North Bridge Inn
Smart TV, fireplace

The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (63 reviews)
"A fantastic stay! Host was very accommodating and quick to respond to messages! Would absolutely stay here again. Our favorite part was the shower with the fun colored lights. Definitely a highlight of our trip! "
United States
Mauri C.
The price is AU$260
includes taxes & fees
9 Mar - 10 Mar
The Pistachio Room at TPH - Boston
Exterior

Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,000 reviews)
"Staff still worked and fed us through a huge snow storm. Really appreciated that"
United States
Keoki
The price is AU$251
includes taxes & fees
8 Mar - 9 Mar
Irving House At Harvard
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
"The area was very nice and the staff were so sweet. The hotel was very clean in all areas.The free WiFi was slow and I had to use my data instead. The surrounding areas were very nice and there was plenty to do and explore "
Dominique 2-night trip
Posted 1 day ago
The Dagny Boston

Find out more about Winchester

Winchester B&B information

Number of reviews
3,540
Accommodation
30 B&B
Lowest Price
AU$180
Highest Price
AU$308

Frequently asked questions

Searching for B&Bs in Winchester?
If you're looking for some accommodation with fewer rooms than the traditional hotel and an intimate environment, a B&B might be just the right fit for your getaway to Winchester. When you want to explore some attractions in town, Winter Pond and Middlesex Fells Reservation are worth a stop.
How do you know if a B&B is the right choice for your stay?
Every B&B has a unique charm — whether it's a picturesque garden or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts a home away from home.
What are the best B&Bs in Winchester?
Here are some well-liked B&Bs in the surrounding area: Homestay In Boston -: 3 rooms. 9.6 mi (15.5 km) from the heart of Winchester. Irving House At Harvard: 5.5 mi (8.8 km) from the city centre. Enjoy the local cuisine breakfast and snack bar/deli. Homestay Near Downtown Boston: 3 rooms. Situated 9.7 mi (15.7 km) from the heart of Winchester. The College Club of Boston: 12 rooms. 7.6 mi (12.2 km) from the city centre. Enjoy the library and coffee shop. Homestay In Fields Corner Area Boston: 11 rooms. Located 11 mi (17.7 km) from the core of Winchester.
When should I stay at a B&B in Winchester?
When you're planning your trip to Winchester, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 13 cm of snowfall.
What is there to do in Winchester?
When you want to see some attractions in town, you might consider a visit to Winter Pond and Middlesex Fells Reservation. You might also consider a trip to sites such as Fenway Park or Encore Boston Harbor if you have time to see more of the area.
How can I get to and around Winchester?
You can plan your excursions in and around Winchester ahead of time with these transportation options. Fly into Bedford, MA (BED-Laurence G. Hanscom Field), which is located 7.7 mi (12.3 km) away from the city centre. Otherwise, you can search for flights to Boston, MA (BNH-Boston Harbor Seaplane Base), which is 8.4 mi (13.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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