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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Winchester bed & breakfast

Full-size fridge, microwave, oven, stovetop
Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
9.4 out of 10, Exceptional, (11)
"The room were clean and staff was courteous. "
United States
Jonathan
The price is AED 253
AED 291 total
includes taxes & fees
11 Jan - 12 Jan
Homestay In Fields Corner Area Boston
Classic Triple Room | Interior
Homestay In Boston -

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
9.0 out of 10, Wonderful, (7)
"Very clean and cozy"
United States
Vladimir
The price is AED 283
AED 325 total
includes taxes & fees
9 Jan - 10 Jan
Homestay In Boston -
Miscellaneous
The College Club of Boston

The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1001)
"Outstanding location, pleasant facilities and staff, decent breakfast choices. "
United States
Mary
The College Club of Boston
Exterior detail
Irving House At Harvard

Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1004)
"Clean, affordable, historic building, little libraries in every room"
United States
Josh
The price is AED 386
AED 441 total
includes taxes & fees
18 Jan - 19 Jan
Irving House At Harvard
Smart TV, fireplace
The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (61)
"Great location and wonderful host"
United States
Robert M.
The price is AED 386
AED 676 total
includes taxes & fees
31 Jan - 1 Feb
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

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (303)
"I enjoy my stay and the room was nice. "
United States
Angel
The price is AED 584
AED 652 total
includes taxes & fees
11 Jan - 12 Jan
The Beacon Waterfront Inn
Exterior
The Salem Inn

The Salem Inn

The Salem Inn
3.5 star property
Salem
9.2 out of 10, Wonderful, (1000)
"Johnny at breakfast was fabulous!! The two that were working with him were awesome too. Johnny recommended the pepper candy store and Turners seafood restaurant were amazing! "
United States
Donna
The price is AED 661
AED 738 total
includes taxes & fees
9 Jan - 10 Jan
The Salem Inn
Front of property
Daniels House Inn

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 AED 819
AED 819 total
includes taxes & fees
16 Jan - 17 Jan
Daniels House Inn
Interior
Homestay Near Downtown Boston

Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
4.0 out of 10, (1)
"If it weren’t for the way the host treated me, this would be a 3–4 star review. The host asks for contact via WhatsApp, which I initially thought was for convenience, but clearly it was so he could be rude outside Expedia’s visibility. I first messaged through Expedia and received no response. When I reached out on WhatsApp with a simple question about luggages, his responses were hostile. He made comments like “make your question intelligible first,” even though my message was polite and...
United States
Amanda Rasera
The price is AED 283
AED 325 total
includes taxes & fees
9 Jan - 10 Jan
Homestay Near Downtown Boston
Front of property
North Bridge Inn

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
10 Jan - 11 Jan
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

Hilton Boston Back Bay

Hilton Boston Back Bay

10/10 Excellent
"Great breakfast, comfortable rooms."
Jiarui 3-night trip
Posted 21 hours ago
Hilton Boston Back Bay

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: The College Club of Boston: 12 rooms. 7.6 mi (12.2 km) from the heart of Winchester. Enjoy the library and coffee shop. Homestay In Boston -: 3 rooms. 9.6 mi (15.5 km) from the downtown core. Homestay In Fields Corner Area Boston: 11 rooms. Situated 11 mi (17.7 km) from the heart of Winchester. Homestay Near Downtown Boston: 3 rooms. 9.7 mi (15.6 km) from the heart of downtown.Irving House At Harvard: Located 5.5 mi (8.8 km) from the core of Winchester. Enjoy the local cuisine breakfast and deli.
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 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 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.