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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 27 B&B in Winchester with updated reviews, rates, and availability.

The Salem Inn
Front of property

The Salem Inn

3.5 star property
9.2 out of 10, Wonderful, (1003)
"Lovely place. Would recommend to others. "
The price is AED 661
AED 739 total
includes taxes & fees
7 Apr - 8 Apr
The Salem Inn
Irving House At Harvard
Exterior detail

Irving House At Harvard

3.0 star property
8.8 out of 10, Excellent, (1002)
"Everyone was so sweet and helpful! I would definitely come back "
The price is AED 863
AED 988 total
includes taxes & fees
12 Apr - 13 Apr
Irving House At Harvard
Homestay BnB Near Downtown Boston
Front of property

Homestay BnB Near Downtown Boston

2.0 star property
8.6 out of 10, Excellent, (34)
"Very clean residence and very close to the city. 10 minute walk from the red line. Would definitely stay again next time I’m in the Boston area."
The price is AED 180
AED 312 total
includes taxes & fees
7 Apr - 8 Apr
Homestay BnB Near Downtown Boston
HomeStay - B&B - Near South Boston - JFK-Umass Area
G1_Wonderful Triple Room With Bathroom | Desk, laptop workspace, free WiFi

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

2.0 star property
9.0 out of 10, Wonderful, (24)
"Clean and quiet. Value for money. To manage your expectations, the floors are very squeaky and the blinds need changing, especially in the shared bathroom."
The price is AED 246
AED 389 total
includes taxes & fees
13 Apr - 14 Apr
HomeStay - B&B - Near South Boston - JFK-Umass Area
The Beacon Waterfront Inn
King Luxury Suite Overlooking the Bay | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe

The Beacon Waterfront Inn

3.0 star property
9.4 out of 10, Exceptional, (279)
"Overall nice stay in the showboat room. Couple things though to mention include that the heat thermostat did not seem to work. We like it a little warmer so we turned it up a bit but the temperature did not change in the room and nor did we hear the heat kick on at all during our stay. It wasn't cold, but it wasn't ideal either -also they only give you a very thin quilt type blanket which during the winter isn't quite enough for me. Other than that, for cleanliness overall facilities looked very...
The price is AED 547
AED 600 total
includes taxes & fees
10 Apr - 11 Apr
The Beacon Waterfront Inn
Château sur Mer Bed & Breakfast
Double Room, 1 Queen Bed | Free WiFi, bed sheets

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 AED 694
AED 775 total
includes taxes & fees
7 Apr - 8 Apr
Château sur Mer Bed & Breakfast
A Village Bed and Breakfast
Front of property

A Village Bed and Breakfast

3.5 star property
10.0 out of 10, Exceptional, (52)
"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
Daniels House Inn
Front of property

Daniels House Inn

3.0 star property
9.6 out of 10, Exceptional, (87)
"The staff was amazing. Stayed in communication the whole time. Clean and walking made easy to almost all shopping and attractions. "
The price is AED 1,127
AED 1,127 total
includes taxes & fees
7 Apr - 8 Apr
Daniels House Inn
North Bridge Inn
Front of property

North Bridge Inn

3.5 star property
8.4 out of 10, Very Good, (347)
"The staff was welcoming and friendly. The room was BEAUTIFUL and breakfast was delicious. Also, the location is perfect! Close to stores, historical sites, and not too far from Boston!"
The price is AED 720
AED 804 total
includes taxes & fees
7 Apr - 8 Apr
North Bridge Inn
In home mini wing private space. 💜Stay at Hal's Salem, MA
Smart TV, video games, DVD player, books

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
Josephine's Bed & Breakfast
View from property

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
The Pistachio Room at TPH - Boston
Outdoor dining

The Pistachio Room at TPH - Boston

9.6 out of 10, Exceptional, (40)
"Comfortable and Clean room with shared living, bathroom, and kitchen. Stayed over Christmas, located a short walk to the bus stop to the train station to downtown. Saw the Lights Display and Bruins Game, love Boston! Advice: bring a pair of slippers since hosts asked for no shoes into the space. "
The price is AED 386
AED 676 total
includes taxes & fees
8 Apr - 9 Apr
The Pistachio Room at TPH - Boston
Stepping Stone Inn
View from property

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, ...
The price is AED 871
AED 973 total
includes taxes & fees
7 Apr - 8 Apr
Stepping Stone Inn
Charming B&B close to Salem and Boston
Private kitchen

Charming B&B close to Salem and Boston

2.0 star property
The price is AED 551
AED 766 total
includes taxes & fees
5 May - 6 May
Charming B&B close to Salem and Boston
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 with WiFi and AC in delightful Somerville
Private kitchen

Charming B&B with WiFi and AC in delightful Somerville

The price is AED 500
AED 730 total
includes taxes & fees
30 Apr - 1 May
Charming B&B with WiFi and AC in delightful Somerville
Wyman Bed & Breakfast
Comfort Room, 1 Bedroom | Premium bedding, cribs/infant beds, rollaway beds, free WiFi

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
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
Fletcher Tavern Bed & Breakfast
Exterior detail

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
Interior detail

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

Sonder 907 Main
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (452)
"Beautiful! What an incredible stay. Completely loved it."
The price is AED 602
AED 698 total
includes taxes & fees
13 Apr - 14 Apr
Sonder 907 Main
Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Living area | 50-inch Smart TV with satellite channels, Netflix, Hulu

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (177)
"Amazing stay, thank you!"
The price is AED 375
AED 790 total
includes taxes & fees
7 Apr - 8 Apr
Maverick Suites at 28 Fenway
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (194)
"The bed is super comfortable, self check in instructions are clear. Microwave, fridge, hairdryer and coffee maker all work excellently. The only downside is the shower hot water takes forever to start, and the heater is very noisy. It’s also close to the road, so the noises from the construction and roads are very noisy. Love the fact there’s elevator. "
The price is AED 436
AED 704 total
includes taxes & fees
24 Apr - 25 Apr
Temple Place Suites
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. HomeStay - B&B - Near South Boston - JFK-Umass Area: 4 rooms. 10.2 mi (16.3 km) from the downtown core. Homestay BnB Near Downtown Boston: 5 rooms. Situated 9.7 mi (15.7 km) from the heart of Winchester. Irving House At Harvard: 5.5 mi (8.8 km) from the heart of downtown. Enjoy the local cuisine breakfast and deli. 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 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.