A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

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Our top choices for Winchester bed & breakfast

The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (75 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 AU$249
includes taxes & fees
3 Aug - 4 Aug
The Pistachio Room at TPH - Boston

Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,002 reviews)
"For the price the private room was good, and the breakfast is better than many places around the BRB."
United States
Ramon
The price is AU$303
includes taxes & fees
27 July - 28 July
Irving House At Harvard

Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
8.0 out of 10, Very good, (68 reviews)
"Great place "
United States
Robert
The price is AU$130
includes taxes & fees
19 Aug - 20 Aug
Homestay In Fields Corner Area Boston

Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
8.2 out of 10, Very good, (28 reviews)
"It was easy to find and beds were comfy price was amazing."
United States
Roscoe
The price is AU$154
includes taxes & fees
26 July - 27 July
Homestay Near Near Savin Hill Area

Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (42 reviews)
"Very clean and tidy, very accommodating with free early check in because our flight arrived so early"
United States
Shannon
The price is AU$110
includes taxes & fees
23 Aug - 24 Aug
Homestay Near Downtown Boston

Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.8 out of 10, Excellent, (221 reviews)
"Beautiful and quiet oasis. Friendly staff and easy check in process. Restaurants were in walking distance and only 28-30 minute drive to the airport. We were able to ise public transit to arrive and found a local cabbie to take us for departure."
United States
Allison
The price is AU$312
includes taxes & fees
24 July - 25 July
Château sur Mer Bed & Breakfast

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.4 out of 10, Very good, (72 reviews)
"Very good set up, very clean room and amenities, would recommend 👍"
United Kingdom
Andrew
The price is AU$192
includes taxes & fees
26 July - 27 July
Homestay In Boston -

Charming B&B close to Salem and Boston

Charming B&B close to Salem and Boston
Lynn
5.8 out of 10, (19 reviews)
"Inexpensive and close to many attractions. "
United States
Maria
Charming B&B close to Salem and Boston

The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1,003 reviews)
"Unique and charming bed and breakfast in a great location."
Canada
Brittany
The price is AU$517
includes taxes & fees
9 Aug - 10 Aug
The College Club of Boston

North Bridge Inn

North Bridge Inn
3.5 star property
Concord
8.4 out of 10, Very good, (352 reviews)
"What a wonderful spot. Nice big rooms, wonderful breakfast and so walkable to Concord. Highly recommend."
United States
Christine
The price is AU$414
includes taxes & fees
17 Aug - 18 Aug
North Bridge Inn

The Salem Inn

The Salem Inn
3.5 star property
Salem
9.4 out of 10, Exceptional, (1,000 reviews)
"Wonderful staff, delicious breakfast and beautiful room!"
United States
Karen
The price is AU$430
includes taxes & fees
26 July - 27 July
The Salem Inn

The Beacon Waterfront Inn

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (322 reviews)
"Everything was perfect I strongly recommended especially the water view.."
United States
Angie
The price is AU$333
includes taxes & fees
26 July - 27 July
The Beacon Waterfront Inn

Homestay BnB Near Downtown Boston

Homestay BnB Near Downtown Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (150 reviews)
"Nice clean room, great for a quick stay! I only needed to be in Boston for one night and this was a great option. 15 minute walk to the Red Line, and it wasn't a bad walk at all. Got back to the place my first night pretty late, but the area was clean and I wasn't nervous about feeling unsafe or anything of that nature. I didn't use the kitchen or some of the other offered amenities but regardless was a pleasant stay. Would definitely come back for any quick trips!"
United States
Ellie
The price is AU$584
includes taxes & fees
24 July - 25 July
Homestay BnB Near Downtown Boston

Stepping Stone Inn

Stepping Stone Inn
2.5 star property
Downtown Salem
9.6 out of 10, Exceptional, (93 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 AU$479
includes taxes & fees
27 July - 28 July
Stepping Stone Inn

Josephine's Bed & Breakfast

Josephine's Bed & Breakfast
3.0 star property
Hull
9.6 out of 10, Exceptional, (128 reviews)
"Beautifully decorated room and wonderful gourmet breakfast made by the wonderful hosts. "
United States
Donald
The price is AU$317
includes taxes & fees
30 July - 31 July
Josephine's Bed & Breakfast

Family friendly home in Hull, steps to downtown and walk to beach!

Family friendly home in Hull, steps to downtown and walk to beach!
Kenberma
The price is AU$995
includes taxes & fees
12 Aug - 13 Aug
Family friendly home in Hull, steps to downtown and walk to beach!
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

Find out more about Winchester

Winchester B&B information

Number of reviews
4,481
Accommodation
36 B&B
Lowest Price
AU$110
Highest Price
AU$584

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: The Salem Inn: 13 mi (21 km) from the heart of Winchester. Enjoy the free cooked breakfast and unique decor. Irving House At Harvard: 5.5 mi (8.8 km) from the city centre. Enjoy the local cuisine breakfast and snack bar/deli. Homestay In Fields Corner Area Boston: 11 rooms. Situated 11 mi (17.7 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 Near Downtown Boston: 3 rooms. Located 9.7 mi (15.7 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 could visit Griffin Photography Museum 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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