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Compare 20 B&B in Winchester with updated reviews, rates, and availability.

The Salem Inn
Front of property

The Salem Inn

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Historical, friendly staff, near everything we needed and complimentary breakfast! "
The price is SAR 635
SAR 709 total
includes taxes & fees
23 Dec - 24 Dec
The Salem Inn
Irving House At Harvard
Exterior detail

Irving House At Harvard

3.0 star property
8.8 out of 10, Excellent, (1003)
"I wounded my forehead reaching for the coffee pot in the basement passageway. You must put some padding there or some sign to explain the risk!"
The price is SAR 432
SAR 580 total
includes taxes & fees
11 Jan - 12 January 2025
Irving House At Harvard
HomeStay - B&B - Near South Boston - JFK-Umass Area
Room

HomeStay - B&B - Near South Boston - JFK-Umass Area

2.0 star property
9.8 out of 10, Exceptional, (11)
"Dan was awesome and has a beautiful home I was very amused by his gratitude and his home. Will stay again. "
The price is SAR 318
SAR 403 total
includes taxes & fees
21 Jan - 22 January 2025
HomeStay - B&B - Near South Boston - JFK-Umass Area
The College Club of Boston
Exterior

The College Club of Boston

3.0 star property
9.2 out of 10, Wonderful, (1002)
"The best place to stay in Boston. But do not spread the word! Keep it a secret! "
The price is SAR 748
SAR 859 total
includes taxes & fees
2 Jan - 3 January 2025
The College Club of Boston
Homestay BnB Near Downtown Boston
Front of property

Homestay BnB Near Downtown Boston

2.0 star property
8.6 out of 10, Excellent, (15)
"What is most important to me is my privacy. I received it with the upmost respect. I hope the owner reads this. I am always critical of something. This will be my first time I found nothing wrong. When in Boston this will be my go to place. Thank you so much for the incredible hospitality! "
The price is SAR 391
SAR 492 total
includes taxes & fees
26 Dec - 27 Dec
Homestay BnB Near Downtown Boston
The Beacon Waterfront Inn
Room

The Beacon Waterfront Inn

3.0 star property
9.4 out of 10, Exceptional, (275)
"Our stay was incredible, the room was more than we hoped for, fire place, deck, huge room, spa tub everything you need for a romantic get away. Our hostess was so sweet and friendly we just can't say enough. We will definitely visit again!"
The price is SAR 597
SAR 655 total
includes taxes & fees
2 Jan - 3 January 2025
The Beacon Waterfront Inn
Morrison House
Front of property

Morrison House

3.0 star property
9.4 out of 10, Exceptional, (49)
"This is a charming B&B located in the heart of Davis Square. The service is excellent! There is home made quick bread (e.g., banana) every morning for breakfast, plus a full array of other breakfast items. French press coffee. Because it's an historic home, the bedrooms are of different sizes. No lift, but the manager kindly carried my suitcase upstairs. There are games and books. I would stay again."
Morrison House
A Village Bed and Breakfast
Room

A Village Bed and Breakfast

3.5 star property
10.0 out of 10, Exceptional, (51)
"delightful breakfast included hard boiled eggs, fresh fruit, yogurt, cereals, cheese, pastries, rustic breads, toaster available, coffee, tea assortment, and much more. nice conversation with owner and other guests during breakfast hour. short walk to train for easy commute into the city. I would stay here again if I come back to the Boston area."
A Village Bed and Breakfast
Josephine's Bed & Breakfast
Room

Josephine's Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (121)
"The parking was up a steep hill but Ann told us ahead of time where to park.The room and common areas are quaint, clean and relaxing."
Josephine's Bed & Breakfast
Château sur Mer Bed & Breakfast
Front of property

Château sur Mer Bed & Breakfast

3.0 star property
8.6 out of 10, Excellent, (201)
"It was a beautiful area, especially this time of year. Joan, our hostess, was very friendly and helpful. Her breakfast was wonderful, and there was plenty of everything. If you left there hungry, it would your own fault. The time I was there I felt at home. Joan was fantastic."
The price is SAR 470
SAR 525 total
includes taxes & fees
6 Jan - 7 January 2025
Château sur Mer Bed & Breakfast
Daniels House Inn
Front of property

Daniels House Inn

3.0 star property
9.4 out of 10, Exceptional, (85)
"My daughter and I really enjoyed our stay here. The location is perfect for walking to everything we wanted to see and on-site parking is a big plus. The place is impeccably clean and having a continental breakfast ready in the morning was a nice touch to start the day. Staying in the oldest house in Salem was a very cool experience. "
Daniels House Inn
Stepping Stone Inn
Exterior

Stepping Stone Inn

2.5 star property
9.6 out of 10, Exceptional, (85)
"Run by the kindest people (and friendliest cats!) in all of Salem, and could not possibly be more centrally located! You can walk everywhere from here, and you have a front row seat to any events in the square - it's literally right across the street. Parking in Salem is at a premium, and we are driving a crew cab truck to make it even worse, but Matt went WELL above and beyond to make sure we got a great spot. Do note - it's a lovely old house, but like most old houses, it does have steps, ...
Stepping Stone Inn
North Bridge Inn
Front of property

North Bridge Inn

3.5 star property
8.4 out of 10, Very Good, (346)
"Excellent. Everything from the smallest detail was covered. Breakfast was wonderful. Bed was very comfortable. Shower was amazing. Everything was top notch! "
The price is SAR 714
SAR 797 total
includes taxes & fees
2 Jan - 3 January 2025
North Bridge Inn
Natalie House - Boston
Front of property

Natalie House - Boston

3.0 star property
8.8 out of 10, Excellent, (26)
"Host was super accommodating. Easy check in. Great neighborhood. "
Natalie House - Boston
Charming B&B close to Salem and Boston
Living area

Charming B&B close to Salem and Boston

2.0 star property
Charming B&B close to Salem and Boston
In home mini wing private space. 💜Stay at Hal's Salem, MA
Exterior

In home mini wing private space. 💜Stay at Hal's Salem, MA

2.0 star property
10.0 out of 10, Exceptional, (2)
"Diane was very accommodating, friendly and offered great suggestions of places to go and see. The little touches, chocolates, stocked fridge, and fruit were so appreciated. The house was decorated so fun! Added to our vibe of a weekend in Salem! We’ll be back! "
In home mini wing private space. 💜Stay at Hal's Salem, MA
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
Wyman Bed & Breakfast
Room

Wyman Bed & Breakfast

2.0 star property
7.4 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
9.0 out of 10, Wonderful, (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
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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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, (30)
"I give this place 3 stars, its a nice place with a good amount of room but there are a few issues. Our stay was Monday - Friday, just 2 adults. Pros - lots of room. Cons - no ac. There is a portable ac unit on wheels in the bedroom however, the exhaust vent goes behind a curtain to the window but not outside. There is no way to open the window for the exhaust vent to take the hot air outside so it just pumps all the hot air back into the room. Be prepared to wake up at 7:30am every morning...
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Sonder 907 Main
Room

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (405)
"Perfect location!"
The price is SAR 483
SAR 560 total
includes taxes & fees
23 Dec - 24 Dec
Sonder 907 Main
Maverick Suites at 28 Fenway
Lobby sitting area

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (156)
"Great stay. "
The price is SAR 372
SAR 795 total
includes taxes & fees
24 Dec - 25 Dec
Maverick Suites at 28 Fenway
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.
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. The College Club of Boston: 12 rooms. Situated 7.6 mi (12.2 km) from the heart of Winchester. Enjoy the library and coffee shop. HomeStay - B&B - Near South Boston - JFK-Umass Area: 4 rooms. 10.2 mi (16.3 km) from the heart of downtown.
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 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 Boston Common or TD Garden 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.