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Our top choices for Winchester bed & breakfast

Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
8.8 out of 10, Excellent, (37 reviews)
"Great place "
United States
Robert
The price is AU$136
includes taxes & fees
21 Apr - 22 Apr
Homestay In Fields Corner Area Boston

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 AU$157
includes taxes & fees
21 Apr - 22 Apr
Homestay Near Downtown Boston

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
9.0 out of 10, Wonderful, (36 reviews)
"Good place for a night. "
United States
René
The price is AU$224
includes taxes & fees
26 Apr - 27 Apr
Homestay In Boston -

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 AU$263
includes taxes & fees
21 Apr - 22 Apr
The Beacon Waterfront Inn

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 AU$280
includes taxes & fees
21 Apr - 22 Apr
The Salem Inn

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 AU$294
includes taxes & fees
21 Apr - 22 Apr
Château sur Mer Bed & Breakfast

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)
"The house was quite very clean awesome place to stay "
United States
Alexadria
The price is AU$167
includes taxes & fees
21 Apr - 22 Apr
Homestay Near Near Savin Hill Area

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 AU$503
includes taxes & fees
21 Apr - 22 Apr
The College Club of Boston

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 AU$305
includes taxes & fees
21 Apr - 22 Apr
Daniels House Inn

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 AU$242
includes taxes & fees
21 Apr - 22 Apr
The Pistachio Room at TPH - Boston

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 AU$319
includes taxes & fees
27 Apr - 28 Apr
North Bridge Inn

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 AU$347
includes taxes & fees
27 Apr - 28 Apr
Stepping Stone Inn

Homestay BnB Near Downtown Boston

Homestay BnB Near Downtown Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (147 reviews)
"Excellent place ..."
United States
Krzysztof
The price is AU$579
includes taxes & fees
21 Apr - 22 Apr
Homestay BnB Near Downtown Boston

Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,008 reviews)
"Cozy room - outstanding breakfast - great location"
United States
Marc
The price is AU$343
includes taxes & fees
29 Apr - 30 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

Find out more about Winchester

Winchester B&B information

Number of reviews
4,140
Accommodation
30 B&B
Lowest Price
AU$136
Highest Price
AU$579

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 Salem Inn: 13 mi (21 km) from the heart of Winchester. Enjoy the free cooked breakfast and unique decor. Irving House At Harvard: 5.5 mi (8.8 km) from the city centre. Enjoy the local cuisine breakfast and snack bar/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 city centre. 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 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 Encore Boston Harbor 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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