Find a Bed and Breakfast in Winchester from CA $134

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Check prices for these dates

Next weekend
May 8 - May 10
In two weeks
May 15 - May 17
In one month
May 29 - May 31
In two months
Jun 26 - Jun 28

Our top choices for Winchester bed & breakfast

Full-size fridge, microwave, oven, stovetop

Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (38 reviews)
"Great place "
United States
Robert
The price is CA $79
CA $134 total
includes taxes & fees
May 7 - May 8
Homestay In Fields Corner Area Boston
Desk, laptop workspace, free WiFi

Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
7.8 out of 10, Good, (11 reviews)
"The house was quite very clean awesome place to stay "
United States
Alexadria
The price is CA $109
CA $137 total
includes taxes & fees
May 7 - May 8
Homestay Near Near Savin Hill Area
Full-size fridge, microwave, oven, stovetop

Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
9.0 out of 10, Wonderful, (23 reviews)
"Great place and friendly host. Host was very accommodating even when we arrived later in the night. Large bedroom with great amenities. Close to public transportation."
United States
Kantinant
The price is CA $80
CA $136 total
includes taxes & fees
May 14 - May 15
Homestay Near Downtown Boston
Full-size fridge, microwave

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.8 out of 10, Excellent, (38 reviews)
"Good place for a night. "
United States
René
The price is CA $113
CA $221 total
includes taxes & fees
May 3 - May 4
Homestay In Boston -
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, (309 reviews)
"Everything was wonderful. Exactly as described. All the little things were perfect, breakfast, housekeeping, snacks, the view, parking, etc.. Location is walking distance from the beach and restaurants, but far enough for quiet privacy. Thank you Cheryl (hope I'm spelling that right), you have a lovely property. Would love to return."
United States
Edward
The price is CA $230
CA $256 total
includes taxes & fees
May 7 - May 8
The Beacon Waterfront Inn
Double Room, 1 Queen Bed

Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.8 out of 10, Excellent, (212 reviews)
"Joan is very friendly and helpful. She seeks to accommodate guests in whatever way she can. My room was quiet and had a private bathroom and shower. I was able to arrive quite late my first night, around 2am, and was left clear instructions on how to get in. Everything was clean and charming. Thanks Joan!"
United States
Jake
The price is CA $257
CA $287 total
includes taxes & fees
May 7 - May 8
Château sur Mer Bed & Breakfast
Exterior

The Salem Inn

The Salem Inn
3.5 star property
Salem
9.2 out of 10, Wonderful, (1,000 reviews)
"Great atmosphere pleasant staff and enjoyed our stay here"
United States
Alexandra
The price is CA $250
CA $279 total
includes taxes & fees
May 3 - May 4
The Salem Inn
Smart TV, fireplace

The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (65 reviews)
"Nice place to live (self catering type) but a slop hill of about 25m to walk through if on foot. With 7 day pass, it is easy to travel to Boston city about 40mins. Nearby, get restaurants and 7-11. It is a good place (cost effective) to stay for my Boston marathon and walk around Boston. "
Hong Kong SAR China
Chin Tung James
The price is CA $128
CA $233 total
includes taxes & fees
May 7 - May 8
The Pistachio Room at TPH - Boston
Front of property

Daniels House Inn

Daniels House Inn
3.0 star property
Salem
9.4 out of 10, Exceptional, (105 reviews)
"It’s a fantastic old house. Great place to stay if you’re looking for a unique experience in Salem"
Canada
Kristofor
The price is CA $417
CA $417 total
includes taxes & fees
May 7 - May 8
Daniels House Inn
Full-size fridge, microwave, oven, stovetop

Homestay BnB Near Downtown Boston

Homestay BnB Near Downtown Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (149 reviews)
"Stayed here for the Boston Marathon as a 23 y/o female and it worked well. The host was kind and responsive. The property was also nice for a home stay situation. I never felt unsafe, each room had a key lock and the bathroom sharing was never a problem. The rooms were spacious and comfortable."
United States
Jenna
The price is CA $180
CA $246 total
includes taxes & fees
May 23 - May 24
Homestay BnB Near Downtown Boston
View from property

Stepping Stone Inn

Stepping Stone Inn
2.5 star property
Downtown Salem
9.6 out of 10, Exceptional, (91 reviews)
"Was great staying at the Stepping Stone, great place, super convenient and amazing staff. Would definitely stay there again."
Canada
Sharon
The price is CA $343
CA $383 total
includes taxes & fees
May 20 - May 21
Stepping Stone Inn
Miscellaneous

The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1,000 reviews)
"Wonderful hospitality, great location!"
United States
Ben
The price is CA $500
CA $575 total
includes taxes & fees
May 3 - May 4
The College Club of Boston
Front of property

North Bridge Inn

North Bridge Inn
3.5 star property
Concord
8.4 out of 10, Very good, (351 reviews)
"Hot breakfast, attentive staff, proximity to a lot of history including Boston"
United States
Martin
The price is CA $352
CA $393 total
includes taxes & fees
May 24 - May 25
North Bridge Inn
Exterior detail

Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,000 reviews)
"Breakfast options were excellent and everything high quality and fresh."
United States
Scott
The price is CA $292
CA $334 total
includes taxes & fees
May 3 - May 4
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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Great stay, very convenient. "
Gary 2-night trip
Posted 2 hours ago
Harborside Inn Of Boston

Find out more about Winchester

Winchester B&B information

Number of reviews
4,354
Accommodation
33 B&B
Lowest Price
CA $134
Highest Price
CA $575

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with a small number of rooms 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?
B&Bs all have a unique charm. Whether it's a picturesque garden or a beautiful dining room, the tiny details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Winchester?
Here are some well-liked B&Bs in the surrounding area: Irving House At Harvard: 5.5 mi (8.8 km) from the heart of Winchester. Enjoy the local cuisine breakfast and deli. The College Club of Boston: 12 rooms. 7.6 mi (12.2 km) from the downtown core. Enjoy the library and coffee shop. Homestay Near Downtown Boston: 3 rooms. Situated 9.7 mi (15.7 km) from the heart of Winchester. The Salem Inn: 13 mi (21 km) from the heart of downtown. Enjoy the free cooked breakfast and unique décor. 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 getaway to Winchester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.
What is there to do in Winchester?
When you want to check out some attractions in town, you might consider a visit to Winter Pond and Middlesex Fells Reservation. You might also consider a trip to sites like 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 map out your trip 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) from the heart of the city. 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 to rent a car for your trip.

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