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Compare B&B in Winchester with updated reviews, rates, and availability.

Irving House At Harvard
Exterior detail
Irving House At Harvard
3.0 star property
8.8 out of 10, Excellent, (1001)
"Was great"
The price is AED 569
AED 736 total
includes taxes & fees
16 Jun - 17 Jun
Irving House At Harvard
The College Club of Boston
Exterior
The College Club of Boston
3.0 star property
9.2 out of 10, Wonderful, (1000)
"The room was tastefully furnished, clean and comfortable. The A /C was a bit noisy however. On the whole, a delightful place; I'd do it again. "
The price is AED 1,282
AED 1,474 total
includes taxes & fees
18 Jun - 19 Jun
The College Club of Boston
The Salem Inn
Front of property
The Salem Inn
3.5 star property
9.0 out of 10, Wonderful, (1001)
"Our stay was wonderful! Would definitely recommend. "
The price is AED 988
AED 1,104 total
includes taxes & fees
18 Jun - 19 Jun
The Salem Inn
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Château sur Mer Bed & Breakfast
Front of property
Château sur Mer Bed & Breakfast
3.0 star property
8.6 out of 10, Excellent, (185)
"Somewhat old fashioned but great location for an over night when flying into or out from Logan. About a $30 Uber ride. "
The price is AED 694
AED 775 total
includes taxes & fees
20 Jun - 21 Jun
Château sur Mer Bed & Breakfast
The Beacon Waterfront Inn
Room
The Beacon Waterfront Inn
3.0 star property
9.4 out of 10, Exceptional, (247)
"The owner of this property was very pleasant . She was attentive to any needs we had during our stay . The room was spotless! We would definately recommend this property to family and friends and stay again. 😊"
The price is AED 768
AED 842 total
includes taxes & fees
17 Jun - 18 Jun
The Beacon Waterfront Inn
A Village Bed and Breakfast
Room
A Village Bed and Breakfast
3.5 star property
10.0 out of 10, Exceptional, (39)
"The room was adorable and homey, staff were absolutely lovely and breakfast was fabulous."
A Village Bed and Breakfast
Morrison House
Front of property
Morrison House
3.0 star property
9.2 out of 10, Wonderful, (42)
"It was exactly what I needed. Thank you!"
Morrison House
Daniels House Inn
Front of property
Daniels House Inn
3.0 star property
9.4 out of 10, Exceptional, (76)
"This was a very unique experience and we're so glad we got to stay here. I booked early to secure the great room. Very spacious room and bathroom. The property is very old but that's what was intriguing to us. Everything in Salem is walkable from here. Would highly recommend! "
The price is AED 1,086
AED 1,086 total
includes taxes & fees
1 Jul - 2 Jul
Daniels House Inn
Stepping Stone Inn
Exterior
Stepping Stone Inn
2.5 star property
9.6 out of 10, Exceptional, (79)
"The hospitality of Matt was amazing. The moment we walked into his beautiful establishment we knew that we made the best choice. When we visit Salem again we will stay no where else. Thank you Matt for the unforgetable experiance "
The price is AED 1,039
AED 1,160 total
includes taxes & fees
15 Jul - 16 Jul
Stepping Stone Inn
North Bridge Inn
Front of property
North Bridge Inn
3.5 star property
8.4 out of 10, Very Good, (344)
"Very tasteful, homey and well appointed without being over the top. We would stay again..."
The price is AED 955
AED 1,067 total
includes taxes & fees
30 Jun - 1 Jul
North Bridge Inn
Josephine's Bed & Breakfast
Room
Josephine's Bed & Breakfast
3.0 star property
9.6 out of 10, Exceptional, (115)
"We had a quick overnight stay but found everything we needed. Breakfast was excellent and the hosts were friendly and welcoming. Highly recommend and would stay again!"
The price is AED 855
AED 855 total
includes taxes & fees
16 Jun - 17 Jun
Josephine's Bed & Breakfast
Chez Pat in Cambridge
Room
Chez Pat in Cambridge
3.0 star property
8.0 out of 10, Very Good, (180)
"Chez Pat has a unique Bostonian setting. A bit of 19th century charm with French furnishing. It is carefully decorated with antiques capturing the history of time and a touch of items from all parts of world. On my desk was a little chest from China. It is such a thoughtful touch. The hotel walls hang many of Pat and her husband paintings. They captured the countryside of France with vivid colors and refined strokes. Ms. Pat came and greeted me herself and made me my breakfast with...
Chez Pat in Cambridge
Old Corner Inn
Exterior
Old Corner Inn
3.0 star property
9.0 out of 10, Wonderful, (38)
"We had a wonderful 1 week stay at the Old Corner Inn! We loved the location. It was less then 2 hours to the train and had great parking! The innkeeper Mike was so friendly and wonderful! He helped us plan our excursions! He went out of his way to make sure our trip was wonderful and special"
Old Corner Inn
Natalie House - Boston
Front of property
Natalie House - Boston
3.0 star property
8.6 out of 10, Excellent, (24)
"It was a very enjoyable and comfortable stay. The owner personally serves her customers and makes them feel at home. My room was spacious and clean. The breakfast was family style; my scrambled eggs were delicious. However the breakfast cost was extra. Also, I didn't have a bathroom in my room, but using the shared bathroom wasn't a problem at all. The area around the hotel is all residential, but you can easily walk to restaurants, transportation, or enjoy the nature near the Boston Reservoir....
Natalie House - Boston
Wyman Bed & Breakfast
Room
Wyman Bed & Breakfast
2.0 star property
7.2 out of 10, Good, (51)
"Aaron went the extra mile to accommodate all the runners over the Boston Marathon Weekend. A fantastic experience, would whole heartedly recommend the Wyman B&B."
Wyman Bed & Breakfast
Fletcher Tavern Bed & Breakfast
Exterior
Fletcher Tavern Bed & Breakfast
4.5 star property
8.8 out of 10, Excellent, (65)
"Had a wonderful stay, Elizabeth is a fantastic hostess, chef, conversationalist and all around humanitarian. Loved all the extra touches you don't get in a hotel, hot tea, organic apples, exquisite soaps, fine books and chimes from antique clocks. I would highly recommend Elizabeth's Tavern to anyone who is looking to experience an immersive "colonial feel" with all the comforts of modern day living."
Fletcher Tavern Bed & Breakfast
Anastasia House
Front of property
Anastasia House
3.0 star property
6.8 out of 10, (10)
"I cannot check in. Nobody at home. The cellphone always lock. I have no idea, if they are fraud？"
Anastasia House
Don't see what you're looking for?
See all available properties in Winchester
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.

Other property types in Winchester

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Private kitchen
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
7.4 out of 10, Good, (28)
"This place was perfect for our Salem visit. Easy to find and convenient for a quick trip to the store. The neighborhood was nice."
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Temple Place Suites
Room
Temple Place Suites
2.5 star property
6.8 out of 10, (92)
"Easily understood instructions for access to building and room. Great location. Bathrooms were not always clean. No windows in room. Good value for price"
The price is AED 436
AED 704 total
includes taxes & fees
30 Jun - 1 Jul
Temple Place Suites
Global Luxury Suites Downtown Boston
Living room
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (421)
"Close to good food and short walks to everywhere we wanted to go. Room seemed recently "Renoed". "
The price is AED 850
AED 1,432 total
includes taxes & fees
16 Jun - 17 Jun
Global Luxury Suites Downtown Boston
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.

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. If your ideal vacation to Winchester includes spending lots of time outside, Middlesex Fells Reservation is a good spot to enjoy the scenery.
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.
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, April, and March, with each month seeing an average of 6 inches of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Middlesex Fells Reservation and Winter Pond are some notable spots. 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.

Recent reviews of Winchester hotels
Expedia verified reviews

The Revolution Hotel

The Revolution Hotel

5/5 Excellent
Wonderful spot
"Wonderful experience for my family of four. Easy to walk all over Boston. The shared bathroom was clean and close by. Would stay there again. "
A verified traveler stayed at The Revolution Hotel
Posted 13 hours ago
The Revolution Hotel