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Check prices for these dates

Next weekend
24 Apr - 26 Apr
In two weeks
1 May - 3 May
In one month
15 May - 17 May
In two months
12 Jun - 14 Jun

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
2.0 star property
Dorchester
8.8 out of 10, Excellent, (36 reviews)
"Great place "
United States
Robert
The price is SAR 123
SAR 250 total
includes taxes & fees
15 Apr - 16 Apr
Homestay In Fields Corner Area Boston
Full-size fridge, microwave, oven, stovetop

Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
9.2 out of 10, Wonderful, (20 reviews)
"Very clean, big rooms. Great breakfast options as well. For someone who just wants a home away from home, this is the place! "
United States
Zakir
The price is SAR 259
SAR 422 total
includes taxes & fees
27 Apr - 28 Apr
Homestay Near Downtown Boston
Full-size fridge, microwave

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
9.0 out of 10, Wonderful, (34 reviews)
"Good place for a night. "
United States
René
The price is SAR 173
SAR 418 total
includes taxes & fees
15 Apr - 16 Apr
Homestay In Boston -
Desk, laptop workspace, free WiFi

Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
7.2 out of 10, Good, (9 reviews)
"Staff was wonderful and helpful. "
United States
Caitlin
The price is SAR 357
SAR 451 total
includes taxes & fees
25 Apr - 26 Apr
Homestay Near Near Savin Hill Area
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, (308 reviews)
"We stayed in the Atlantic sweet. It was beautiful, along with the rest of the inn. Very welcoming, peaceful and comfortable. Will be back! "
United States
Keagan
The price is SAR 634
SAR 708 total
includes taxes & fees
16 Apr - 17 Apr
The Beacon Waterfront Inn
Exterior

The Salem Inn

The Salem Inn
3.5 star property
Salem
9.2 out of 10, Wonderful, (1,000 reviews)
"Our stay was wonderful! Staff was attentive and friendly. The rooms were very nice and the bed was comfortable. Breakfast was delicious and a great send off. We will visit again. "
United States
Anthony
The price is SAR 675
SAR 755 total
includes taxes & fees
22 Apr - 23 Apr
The Salem Inn
Double Room, 1 Queen Bed | Free WiFi, bed sheets

Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.6 out of 10, Excellent, (211 reviews)
"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 SAR 709
SAR 792 total
includes taxes & fees
15 Apr - 16 Apr
Château sur Mer Bed & Breakfast
Front of property

Daniels House Inn

Daniels House Inn
3.0 star property
Salem
9.4 out of 10, Exceptional, (104 reviews)
"Clearly a well managed historic inn. Gorgeous, comfortable, unique, in a very walkable area. "
United States
April
The price is SAR 724
SAR 724 total
includes taxes & fees
16 Apr - 17 Apr
Daniels House Inn
Miscellaneous

The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1,004 reviews)
"We loved our stay. Everything was close by very convenient location and friendly staff too"
United States
Judith
The price is SAR 942
SAR 1,083 total
includes taxes & fees
15 Apr - 16 Apr
The College Club of Boston
Smart TV, fireplace

The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (63 reviews)
"A fantastic stay! Host was very accommodating and quick to respond to messages! Would absolutely stay here again. Our favorite part was the shower with the fun colored lights. Definitely a highlight of our trip! "
United States
Mauri C.
The price is SAR 394
SAR 690 total
includes taxes & fees
6 May - 7 May
The Pistachio Room at TPH - Boston
Front of property

North Bridge Inn

North Bridge Inn
3.5 star property
Concord
8.4 out of 10, Very Good, (350 reviews)
"Hot breakfast, attentive staff, proximity to a lot of history including Boston"
United States
Martin
The price is SAR 732
SAR 817 total
includes taxes & fees
29 Apr - 30 Apr
North Bridge Inn
View from property

Stepping Stone Inn

Stepping Stone Inn
2.5 star property
Downtown Salem
9.6 out of 10, Exceptional, (91 reviews)
"Cute place clean and walkable to everything. Nice staff"
United States
Christine
The price is SAR 836
SAR 933 total
includes taxes & fees
15 Apr - 16 Apr
Stepping Stone Inn
Exterior detail

Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,005 reviews)
"Cozy room - outstanding breakfast - great location"
United States
Marc
The price is SAR 995
SAR 1,138 total
includes taxes & fees
21 Apr - 22 Apr
Irving House At Harvard
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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"No breakfast. Beds are super comfy. "
Fabiola brione 3-night trip
Posted 2 hours ago
Omni Boston Hotel at the Seaport

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 Salem Inn: 13 mi (21 km) from the heart of Winchester. Enjoy the free cooked breakfast and unique décor. Irving House At Harvard: 5.5 mi (8.8 km) from the downtown core. Enjoy the local cuisine breakfast and deli. Homestay Near Downtown Boston: 3 rooms. Situated 9.7 mi (15.7 km) from the heart of Winchester. Homestay In Boston -: 3 rooms. 9.6 mi (15.5 km) from the heart of downtown.The College Club of Boston: 12 rooms. Located 7.6 mi (12.2 km) from the core of Winchester. Enjoy the library and coffee shop.
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 Encore Boston Harbor 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.

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