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Compare 19 B&B in Winchester with updated reviews, rates, and availability.

Irving House At Harvard
3.0 star property
8.8 out of 10, Excellent, (1004)
"I just really enjoyed the neighborhood vibe. I was ur only there for night but could have stayed much longer "
The price is SAR 581
SAR 665 total
includes taxes & fees
1 Raj. - 2 Raj.
Irving House At Harvard
The College Club of Boston
3.0 star property
9.2 out of 10, Wonderful, (1000)
"Lovely place!"
The price is SAR 971
SAR 1,117 total
includes taxes & fees
1 Raj. - 2 Raj.
The College Club of Boston
The Salem Inn
3.5 star property
9.0 out of 10, Wonderful, (1000)
"This is a BnB in historic homes, each room is different. Our room was quaint, spacious, clean and quiet. We had a bay window, fireplace and canopy bed. The bath had a relaxing whirlpool tub. The location of this hotel is great. You can park your car in the provided parking lot and walk to most all the sights and restaurants. The staff was helpful. The breakfast portion of the BnB needs an upgrade-I felt the food was the same as buffet breakfast food you receive at a moderate hotel chain,...
The price is SAR 1,009
SAR 1,127 total
includes taxes & fees
2 Jum. II - 3 Jum. II
The Salem Inn
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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 SAR 709
SAR 792 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Château sur Mer Bed & Breakfast
The Beacon Waterfront Inn
3.0 star property
9.4 out of 10, Exceptional, (245)
"Bugs"
The price is SAR 709
SAR 778 total
includes taxes & fees
2 Jum. II - 3 Jum. II
The Beacon Waterfront Inn
A Village Bed and Breakfast
3.5 star property
10.0 out of 10, Exceptional, (36)
"Friendly and helpful host. Fabulous breakfast and great coffee. She grinds the beans! Charming home and walkable neighborhood with restaurants nearby."
A Village Bed and Breakfast
Morrison House
3.0 star property
9.2 out of 10, Wonderful, (41)
"A great find, very cozy, but not chintzy at all. Rooms comfortable, very quiet neighborhood, parking available, very close to the T, nice walkable, downtown, easy to get to, nice breakfast, helpful but unintrusive hosts, and an adorable cat!"
Morrison House
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 SAR 971
SAR 1,084 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Stepping Stone Inn
Daniels House Inn
3.0 star property
9.4 out of 10, Exceptional, (73)
"We really like staying at unique or historical properties. The Daniels house was both. The Hostess at breakfast was very friendly and helpful with our questions about parking for my brother who was coming to meet us. Would stay here again. The only con would be thevceiling height in the 3rd floor rooms."
The price is SAR 1,049
SAR 1,049 total
includes taxes & fees
30 Jum. II - 1 Raj.
Daniels House Inn
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 SAR 975
SAR 1,089 total
includes taxes & fees
12 Jum. II - 13 Jum. II
North Bridge Inn
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 SAR 878
SAR 878 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Josephine's Bed & Breakfast
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
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
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....
The price is SAR 1,009
SAR 1,217 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Natalie House - Boston
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
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
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
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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
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
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (413)
"Decent place"
The price is SAR 1,009
SAR 1,628 total
includes taxes & fees
9 Jum. II - 10 Jum. II
Global Luxury Suites Downtown Boston
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2210)
"I’ve stayed here a few times now. Always a good experience."
The price is SAR 638
SAR 712 total
includes taxes & fees
1 Raj. - 2 Raj.
HYATT house Boston/Burlington
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, Winter Pond and Middlesex Fells Reservation 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.

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