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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Check prices for these dates

Next weekend
18 Sept - 20 Sept
In two weeks
25 Sept - 27 Sept
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 Nov

Our top choices for Winchester bed & breakfast

Shared kitchen

1. Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.2 out of 10, Very good, (94 reviews)
"I really enjoyed my time there"
United States
Markessee
The price is AU$134
includes taxes & fees
21 Sept - 22 Sept
Homestay In Boston -
Shared kitchen

2. Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
7.6 out of 10, Good, (78 reviews)
"It was a weird place"
United States
Gema
The price is AU$141
includes taxes & fees
9 Sept - 10 Sept
Homestay In Fields Corner Area Boston
Exterior detail

3. Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,002 reviews)
"Irving House is in a good location close to what we wanted to see. Breakfast was good with lots of choices. There is a laundry area but we did not use it. Quiet at night. I’m BeReal we would stay there again."
United States
Sue
The price is AU$294
includes taxes & fees
10 Sept - 11 Sept
Irving House At Harvard
Room

4. Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
7.8 out of 10, Good, (51 reviews)
"Very well kept property"
United States
simone
The price is AU$153
includes taxes & fees
9 Sept - 10 Sept
Homestay Near Near Savin Hill Area
Shared kitchen

5. Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.4 out of 10, Very good, (51 reviews)
"This is a great low cost option. I only needed to spend one night, but would consider longer stays in the future, especially since there is access to a kitchen."
United States
Patrick
The price is AU$138
includes taxes & fees
9 Sept - 10 Sept
Homestay Near Downtown Boston
Double Room, 1 Queen Bed

6. Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.6 out of 10, Excellent, (223 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$256
includes taxes & fees
14 Sept - 15 Sept
Château sur Mer Bed & Breakfast
Living area

7. The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (77 reviews)
"There room and common areas were very clean neat. It was a very pleasant stay. I would stay there again."
United States
L M C.
The price is AU$258
includes taxes & fees
4 Oct - 5 Oct
The Pistachio Room at TPH - Boston
Living area

8. 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
The price is AU$292
includes taxes & fees
6 Oct - 7 Oct
Charming B&B close to Salem and Boston
Private kitchen

9. 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$232
includes taxes & fees
19 Sept - 20 Sept
Homestay BnB Near Downtown Boston
Double Room, Ensuite

10. 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)
"Delightful and charming stay."
United States
Hannah
The price is AU$573
includes taxes & fees
10 Sept - 11 Sept
The College Club of Boston
King Luxury Suite Overlooking the Bay

11. The Beacon Waterfront Inn

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (328 reviews)
"The room was incredible, very clean and the staff was wonderful"
United States
Sarah
The price is AU$262
includes taxes & fees
13 Sept - 14 Sept
The Beacon Waterfront Inn
Exterior detail

12. 2-bedroom bed & breakfast in adorable Lynn with AC comfort

2-bedroom bed & breakfast in adorable Lynn with AC comfort
Lynn
The price is AU$511
includes taxes & fees
14 Sept - 15 Sept
2-bedroom bed & breakfast in adorable Lynn with AC comfort
View from property

13. Josephine's Bed & Breakfast

Josephine's Bed & Breakfast
3.0 star property
Hull
9.6 out of 10, Exceptional, (133 reviews)
"Josephines was lovely. Very nostalgic, loved the decor!!! Breakfast was excellent! I am hoping to stay there again"
United States
Marsha
The price is AU$257
includes taxes & fees
9 Sept - 10 Sept
Josephine's Bed & Breakfast
Front of property

14. Daniels House Inn

Daniels House Inn
3.0 star property
Salem
9.4 out of 10, Exceptional, (117 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 AU$412
includes taxes & fees
9 Sept - 10 Sept
Daniels House 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

The Revolution Hotel

The Revolution Hotel

8/10 Good
"The location is great, very close to public transit. The room was cute and had all the necessities (was in a queen room with private bath). Front desk staff was pleasant. My only gripe was the presence of gnats in the shower drain that would fly up and out when I tried to bathe. The room itself was relatively clean besides some dust bunnies behind the sliding bathroom door, but the gnats in the shower could definitely use some attention. Highly suggest an enzymatic drain maintainer. A decent place overall!"
Kaylee 2-night trip
Posted 1 hour ago
The Revolution Hotel

Find out more about Winchester

Winchester B&B information

Number of reviews
3,083
Accommodation
36 B&B
Lowest Price
AU$134
Highest Price
AU$573

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, Griffin Photography Museum and Winter Pond 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: Irving House At Harvard: 5.5 mi (8.8 km) from the heart of Winchester. Enjoy the local cuisine breakfast and snack bar/deli. Homestay In Boston -: 3 rooms. 9.6 mi (15.5 km) from the city centre. The College Club of Boston: 12 rooms. Situated 7.6 mi (12.2 km) from the heart of Winchester. Enjoy the unique decor and library. Homestay Near Near Savin Hill Area: 8 rooms. 10.3 mi (16.6 km) from the city centre. 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?
If you're looking to find something to do during your travels, you might consider visiting Griffin Photography Museum and Winter Pond. You could visit Middlesex Fells Reservation 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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