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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Featured B&B in Winchester

Classic Triple Room | Interior
Homestay In Boston -

Homestay In Boston -

2.0 star property
Dorchester
The price is AU$109
includes taxes & fees
15 Dec - 16 Dec
Homestay In Boston -
Standard Double Room | Interior
Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston

2.0 star property
Dorchester
10.0 out of 10, Exceptional, (1)
"Great house!"
United States
Liang
The price is AU$72
includes taxes & fees
21 Dec - 22 Dec
Homestay In Fields Corner Area Boston
Miscellaneous
The College Club of Boston

The College Club of Boston

3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1001)
"Everything! Tbh my fave was the cookies! It was the perfect stay in the heart of it all while being super quiet for a solo traveler! "
United States
Haley
The price is AU$265
includes taxes & fees
4 Jan - 5 Jan 2026
The College Club of Boston
Exterior
Homestay Near Downtown Boston

Homestay Near Downtown Boston

2.0 star property
Dorchester
The price is AU$134
includes taxes & fees
15 Dec - 16 Dec
Homestay Near Downtown Boston
Exterior detail
Irving House At Harvard

Irving House At Harvard

3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1008)
"nice but very small room, staff very good"
United States
Francesco
The price is AU$234
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, (60)
"Great location and wonderful host"
United States
Robert M.
The price is AU$263
includes taxes & fees
17 Dec - 18 Dec
The Pistachio Room at TPH - 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, (301)
"Beautiful spacious room "
United States
Maryann
The price is AU$252
includes taxes & fees
1 Jan - 2 Jan 2026
The Beacon Waterfront Inn
Front of property
The Salem Inn

The Salem Inn

3.5 star property
Salem
9.2 out of 10, Wonderful, (1000)
"Very clean and lovely atmosphere! Definitely grateful to stay here so I could walk everywhere! All the cool places are in walking distance."
United States
Chelsey
The price is AU$304
includes taxes & fees
10 Dec - 11 Dec
The Salem Inn
Front of property
Daniels House Inn

Daniels House Inn

3.0 star property
Salem
9.4 out of 10, Exceptional, (100)
"This property is amazing. The home and rooms are clean, comfortable and beautiful. "
United States
Rachel
The price is AU$415
includes taxes & fees
7 Dec - 8 Dec
Daniels House Inn
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 AU$330
includes taxes & fees
1 Jan - 2 Jan 2026
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

The Dagny Boston

The Dagny Boston

10/10 Excellent
"Beautiful room design, clean and super quiet area. Will stay again"
John 2-night trip
Posted 2 days ago
The Dagny Boston

Find out more about Winchester

Winchester B&B information

Number of reviews
3,511
Accommodation
28 B&B
Lowest Price
AU$234
Highest Price
AU$415

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 College Club of Boston: 12 rooms. 7.6 mi (12.2 km) from the heart of Winchester. Enjoy the library and coffee shop. Irving House At Harvard: 5.5 mi (8.8 km) from the city centre. Enjoy the local cuisine breakfast and snack bar/deli. 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 city centre. Enjoy the free cooked breakfast and unique decor. 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 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 might also consider a trip to sites such as 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 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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