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Check prices for these dates

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured B&B in Winchester

Front of property
Homestay BnB Near Downtown Boston
Homestay BnB Near Downtown Boston
2.0 star property
8.6 out of 10, Excellent, (106)
"Clean space Worked well for our short stay in Boston "
United States
HAYLEY
The price is AU$198
includes taxes & fees
2 Nov - 3 Nov
Homestay BnB Near Downtown Boston
Exterior
The College Club of Boston
The College Club of Boston
3.0 star property
9.4 out of 10, Exceptional, (1004)
"Great location. Perfect for my short stay for business. "
United States
Oscar
The price is AU$529
includes taxes & fees
16 Nov - 17 Nov
The College Club of Boston
Property grounds
The Pistachio Room at TPH - Boston
The Pistachio Room at TPH - Boston
9.6 out of 10, Exceptional, (55)
"We stayed here while at our son's Boston College location. Everything was well maintained, especially for being such an older, historic house, and the location was conveniently located."
United States
Robert F.
The price is AU$268
includes taxes & fees
20 Oct - 21 Oct
The Pistachio Room at TPH - Boston
King Luxury Suite Overlooking the Bay
The Beacon Waterfront Inn
The Beacon Waterfront Inn
3.0 star property
9.4 out of 10, Exceptional, (296)
"Fantastic room definitely recommend staying here Next time would like to try the Atlantic room "
United Kingdom
Derrick
The price is AU$268
includes taxes & fees
26 Oct - 27 Oct
The Beacon Waterfront Inn
Front of property
The Salem Inn
The Salem Inn
3.5 star property
9.2 out of 10, Wonderful, (1000)
"Very quaint and excellent location"
United States
Mary
The price is AU$320
includes taxes & fees
11 Nov - 12 Nov
The Salem Inn
Exterior detail
Irving House At Harvard
Irving House At Harvard
3.0 star property
9.0 out of 10, Wonderful, (1011)
"Great location"
United States
Thomas
The price is AU$396
includes taxes & fees
9 Nov - 10 Nov
Irving House At Harvard
View from property
Josephine's Bed & Breakfast
Josephine's Bed & Breakfast
3.0 star property
9.6 out of 10, Exceptional, (125)
"AnnMarie made my stay relaxing and comfortable. I felt very at home. I can't wait to be back. "
United States
Ashley
The price is AU$279
includes taxes & fees
22 Oct - 23 Oct
Josephine's Bed & Breakfast
Double Room, 1 Queen Bed
Château sur Mer Bed & Breakfast
Château sur Mer Bed & Breakfast
3.0 star property
8.8 out of 10, Excellent, (209)
"Very quaint and cute bed and breakfast with fun view of the bay and airplanes landing, cute restaurants nearby and super close to the airport. Great price for accommodations near Logan for early morning flight."
United States
Heidi
The price is AU$325
includes taxes & fees
21 Oct - 22 Oct
Château sur Mer Bed & Breakfast
Front of property
Daniels House Inn
Daniels House Inn
3.0 star property
9.4 out of 10, Exceptional, (98)
"Absolutely one of a kind historic home - it ended up being the very best part of our trip. The housekeeper was lovely, the breakfast and decor are thoughtful and elegant."
United States
Elizabeth
The price is AU$506
includes taxes & fees
16 Nov - 17 Nov
Daniels House Inn
Basic Room | Bathroom
HomeStay - B&B - Near South Boston - JFK-Umass Area
HomeStay - B&B - Near South Boston - JFK-Umass Area
2.0 star property
8.4 out of 10, Very good, (57)
"Loved this stay!"
United States
Youngim
HomeStay - B&B - Near South Boston - JFK-Umass Area
Private kitchen
Charming B&B close to Salem and Boston
Charming B&B close to Salem and Boston
2.0 star property
5.2 out of 10, (10)
"Very quiet at night was great for resting. Great place to visit and stay. "
United States
Orlando M.
The price is AU$333
includes taxes & fees
23 Oct - 24 Oct
Charming B&B close to Salem and Boston
Front of property
North Bridge Inn
North Bridge Inn
3.5 star property
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$335
includes taxes & fees
11 Nov - 12 Nov
North Bridge Inn
Outdoor spa tub
In home mini wing private space. 💜Stay at Hal's Salem, MA
In home mini wing private space. 💜Stay at Hal's Salem, MA
2.0 star property
10.0 out of 10, Exceptional, (9)
"This place was so clean, safe, and wonderful in all aspects. Highly recommended. Views out back of beautiful gardens and Marsh. There was a great assortment of snacks, movies, games, and books.Host family lives here and were so pleasant and welcoming. Book this listing today! You wont be disappointed. "
United States
Nancy
The price is AU$1,192
includes taxes & fees
29 Oct - 30 Oct
In home mini wing private space. 💜Stay at Hal's Salem, MA
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
"Enjoyed our stay very much. Everyone that worked at the hotel helpful. Room was a little small but very clean. Housekeeping services - outstanding. My only complaint was about the pillows. Asked for foam instead of feather and the foam pillows were terrible!!!!! Buy some new ones. Also, location can’t be beat!!"
Ginette 4-night trip
Posted 19 hours ago
The Dagny Boston

Find out more about Winchester

Winchester B&B information

Number of reviews
3,993
Accommodation
28 B&B
Lowest Price
AU$198
Highest Price
AU$1,192

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, Middlesex Fells Reservation 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 BnB Near Downtown Boston: 5 rooms. 9.7 mi (15.7 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 library and coffee shop. HomeStay - B&B - Near South Boston - JFK-Umass Area: 4 rooms. Located 10.2 mi (16.3 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 Middlesex Fells Reservation and Winter Pond. You might also consider a trip to sites such as TD Garden or Fenway Park 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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