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Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

B&B in Winchester

Front of property
Homestay BnB Near Downtown Boston

Homestay BnB Near Downtown Boston

2.0 star property
Dorchester
8.4 out of 10, Very Good, (125)
"Thank you perfect place to stay "
United States
Iuliia
The price is AED 116
AED 239 total
includes taxes & fees
18 Nov - 19 Nov
Homestay BnB Near Downtown Boston
Exterior
The College Club of Boston

The College Club of Boston

3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1000)
"It was awesome!!"
United States
Takuya
The College Club of Boston
Exterior detail
Irving House At Harvard

Irving House At Harvard

3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1001)
"nice but very small room, staff very good"
United States
Francesco
The price is AED 496
AED 568 total
includes taxes & fees
17 Dec - 18 Dec
Irving House At Harvard
Property grounds
The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston

Brighton
9.6 out of 10, Exceptional, (58)
"Great location and wonderful host"
United States
Robert M.
The price is AED 347
AED 631 total
includes taxes & fees
18 Nov - 19 Nov
The Pistachio Room at TPH - Boston
King Luxury Suite Overlooking the Bay | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Beacon Waterfront Inn

The Beacon Waterfront Inn

3.0 star property
Hull
9.4 out of 10, Exceptional, (300)
"I enjoy my stay and the room was nice. "
United States
Angel
The price is AED 621
AED 681 total
includes taxes & fees
20 Nov - 21 Nov
The Beacon Waterfront Inn
Front of property
Daniels House Inn

Daniels House Inn

3.0 star property
Salem
9.4 out of 10, Exceptional, (99)
"This property is amazing. The home and rooms are clean, comfortable and beautiful. "
United States
Rachel
The price is AED 1,006
AED 1,006 total
includes taxes & fees
2 Dec - 3 Dec
Daniels House Inn
Front of property
The Salem Inn

The Salem Inn

3.5 star property
Salem
9.2 out of 10, Wonderful, (1002)
"Very quaint and excellent location"
United States
Mary
The price is AED 661
AED 738 total
includes taxes & fees
20 Nov - 21 Nov
The Salem Inn
Private kitchen
Charming B&B close to Salem and Boston

Charming B&B close to Salem and Boston

2.0 star property
Lynn
5.8 out of 10, (15)
"Very quiet at night was great for resting. Great place to visit and stay. "
United States
Orlando M.
The price is AED 551
AED 782 total
includes taxes & fees
18 Nov - 19 Nov
Charming B&B close to Salem and Boston
Front of property
North Bridge Inn

North Bridge Inn

3.5 star property
Concord
8.4 out of 10, Very Good, (349)
"Hot breakfast, attentive staff, proximity to a lot of history including Boston"
United States
Martin
The price is AED 716
AED 800 total
includes taxes & fees
30 Nov - 1 Dec
North Bridge 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

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Staff ,food,design,housekeeping,arriving through leaving all superb. Thanks for the great stay."
Jan 2-night trip
Posted 12 hours ago
Seaport Hotel Boston

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 BnB Near Downtown Boston: 5 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. Charming B&B close to Salem and Boston: Located 9.9 mi (15.9 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 Harvard Square 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.