Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.

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Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16

Our top choices for Winchester bed & breakfast

Soap, shampoo, toilet paper

Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
8.2 out of 10, Very good, (55 reviews)
"Great place "
United States
Robert
The price is CA $147
CA $169 total
includes taxes & fees
Jul 12 - Jul 13
Homestay In Fields Corner Area Boston
Full-size fridge, microwave, oven, stovetop

Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (31 reviews)
"Room was simple but clean. Provision for breakfast and availability of kitchen area was appreciated."
United States
Lawrence
The price is CA $97
CA $111 total
includes taxes & fees
Jul 2 - Jul 3
Homestay Near Downtown Boston
Free toiletries, towels, soap, shampoo

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.4 out of 10, Very good, (56 reviews)
"I like to have my own room, and not so much sharing a bathroom, but this is the price you pay for a budget lodging."
United States
Ramon
The price is CA $157
CA $213 total
includes taxes & fees
Jun 17 - Jun 18
Homestay In Boston -
Superior Suite w/ Hot Tub and Fireplace | Bathroom

The Beacon Waterfront Inn

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (312 reviews)
"Everything was perfect I strongly recommended especially the water view.."
United States
Angie
The price is CA $238
CA $266 total
includes taxes & fees
Jun 24 - Jun 25
The Beacon Waterfront Inn
Living area

Charming B&B close to Salem and Boston

Charming B&B close to Salem and Boston
Lynn
5.8 out of 10, (16 reviews)
"Inexpensive and close to many attractions. "
United States
Maria
The price is CA $210
CA $296 total
includes taxes & fees
Jun 24 - Jun 25
Charming B&B close to Salem and Boston
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, (213 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 $306
CA $342 total
includes taxes & fees
Jul 6 - Jul 7
Château sur Mer Bed & Breakfast
Exterior

The Salem Inn

The Salem Inn
3.5 star property
Salem
9.4 out of 10, Exceptional, (1,000 reviews)
"Very pleasant period building, with modern amenities. Had a great stay."
United States
Terry
The price is CA $376
CA $420 total
includes taxes & fees
Jul 8 - Jul 9
The Salem Inn
View from property

Josephine's Bed & Breakfast

Josephine's Bed & Breakfast
3.0 star property
Hull
9.6 out of 10, Exceptional, (127 reviews)
"Very clean and safe. Plenty of parking available and the Sober Peach Melba was delicious!"
United States
Lyndi
The price is CA $346
CA $346 total
includes taxes & fees
Jun 24 - Jun 25
Josephine's Bed & Breakfast
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 $189
CA $258 total
includes taxes & fees
Jul 3 - Jul 4
Homestay BnB Near Downtown Boston
Smart TV, fireplace

The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (70 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 $183
CA $301 total
includes taxes & fees
Jun 24 - Jun 25
The Pistachio Room at TPH - Boston
Double Room, Ensuite

The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1,004 reviews)
"great location"
United States
Gines Diego
The price is CA $439
CA $505 total
includes taxes & fees
Jul 13 - Jul 14
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)
"What a wonderful spot. Nice big rooms, wonderful breakfast and so walkable to Concord. Highly recommend."
United States
Christine
The price is CA $362
CA $405 total
includes taxes & fees
Jun 17 - Jun 18
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, (1,008 reviews)
"Nice food, place and people "
United States
Priscilla
The price is CA $301
CA $344 total
includes taxes & fees
Jun 30 - Jul 1
Irving House At Harvard
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 $463
CA $517 total
includes taxes & fees
Jul 6 - Jul 7
Stepping Stone 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 Parker House

Omni Parker House

10/10 Excellent
"Excellent Hotel."
Paul 2-night trip
Posted 7 hours ago
Omni Parker House

Find out more about Winchester

Winchester B&B information

Number of reviews
4,483
Accommodation
33 B&B
Lowest Price
CA $111
Highest Price
CA $517

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: Homestay In Fields Corner Area Boston: 11 rooms. 11 mi (17.7 km) from the heart of Winchester.Irving House At Harvard: 5.5 mi (8.8 km) from the downtown core. Enjoy the local cuisine breakfast and deli. The Salem Inn: Situated 13 mi (21 km) from the heart of Winchester. Enjoy the free cooked breakfast and unique décor. Homestay Near Downtown Boston: 3 rooms. 9.7 mi (15.7 km) from the heart of downtown.Homestay In Boston -: 3 rooms. Located 9.6 mi (15.5 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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