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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured B&B in Winchester

Irving House At Harvard
Exterior detail

Irving House At Harvard

3.0 star property
8.8 out of 10, Excellent, (1003)
"Nice friendly atmosphere, great breakfast "
The price is AU$360
includes taxes & fees
27 July - 28 July
Irving House At Harvard
The Salem Inn
Front of property

The Salem Inn

3.5 star property
9.2 out of 10, Wonderful, (1000)
"Great location and comfortable!"
The price is AU$384
includes taxes & fees
29 July - 30 July
The Salem Inn
Homestay BnB Near Downtown Boston
Front of property

Homestay BnB Near Downtown Boston

2.0 star property
8.6 out of 10, Excellent, (69)
"It was a very convenient location very close to the T Station"
The price is AU$235
includes taxes & fees
23 July - 24 July
Homestay BnB Near Downtown Boston
The College Club of Boston
Miscellaneous

The College Club of Boston

3.0 star property
9.2 out of 10, Wonderful, (1006)
"My daughter and I loved our stay! It was very convenient to the Boston Public Garden and Common with lots of food options nearby. Amazing old building and a great cause to support! "
The price is AU$580
includes taxes & fees
27 July - 28 July
The College Club of Boston
The Beacon Waterfront Inn
King Luxury Suite Overlooking the Bay

The Beacon Waterfront Inn

3.0 star property
9.4 out of 10, Exceptional, (289)
"Cheryl was a lovely host. I enjoyed my stay:)"
The price is AU$351
includes taxes & fees
23 July - 24 July
The Beacon Waterfront Inn
HomeStay - B&B - Near South Boston - JFK-Umass Area
Basic Room | Bathroom

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

2.0 star property
8.4 out of 10, Very good, (45)
"Close to the train, good for a short stay"
HomeStay - B&B - Near South Boston - JFK-Umass Area
Daniels House Inn
Front of property

Daniels House Inn

3.0 star property
9.6 out of 10, Exceptional, (94)
"Amazing atmosphere and location! The owners had quick and thorough communication. "
The price is AU$487
includes taxes & fees
27 July - 28 July
Daniels House Inn
Morrison House
Exterior

Morrison House

3.0 star property
9.4 out of 10, Exceptional, (51)
"Very pleasant stay"
Morrison House
Château sur Mer Bed & Breakfast
Double Room, 1 Queen Bed

Château sur Mer Bed & Breakfast

3.0 star property
8.6 out of 10, Excellent, (204)
"I"
The price is AU$324
includes taxes & fees
26 July - 27 July
Château sur Mer Bed & Breakfast
The Pistachio Room at TPH - Boston
Property grounds

The Pistachio Room at TPH - Boston

9.6 out of 10, Exceptional, (48)
"Decent Stay"
The price is AU$342
includes taxes & fees
12 Aug - 13 Aug
The Pistachio Room at TPH - Boston
Charming B&B close to Salem and Boston
Private kitchen

Charming B&B close to Salem and Boston

2.0 star property
5.6 out of 10, (5)
The price is AU$303
includes taxes & fees
23 July - 24 July
Charming B&B close to Salem and Boston
A Village Bed and Breakfast
Front of property

A Village Bed and Breakfast

3.5 star property
10.0 out of 10, Exceptional, (56)
"Wonderful service from the young lady who took care of the house. Delicious breakfast! Safe neighborhood. Lovely location. "
A Village Bed and Breakfast
Stepping Stone Inn
View from property

Stepping Stone Inn

2.5 star property
9.6 out of 10, Exceptional, (85)
"Was great staying at the Stepping Stone, great place, super convenient and amazing staff. Would definitely stay there again."
The price is AU$513
includes taxes & fees
28 July - 29 July
Stepping Stone Inn
North Bridge Inn
Front of property

North Bridge Inn

3.5 star property
8.4 out of 10, Very good, (348)
"Hot breakfast, attentive staff, proximity to a lot of history including Boston"
The price is AU$443
includes taxes & fees
6 Aug - 7 Aug
North Bridge Inn
Josephine's Bed & Breakfast
View from property

Josephine's Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (123)
"Family and historical artifacts throughout"
The price is AU$358
includes taxes & fees
24 July - 25 July
Josephine's Bed & Breakfast
"The In & Out Room" at TPH - Boston
Fridge, microwave, oven, stovetop

"The In & Out Room" at TPH - Boston

10.0 out of 10, Exceptional, (11)
"Beautifully appointed guest property. Host has attended to every detail to make guests comfortable."
"The In & Out Room" at TPH - Boston
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)
In home mini wing private space. 💜Stay at Hal's Salem, MA
Natalie House - Boston
Garden

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
Old Corner Inn
Free self-parking

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
Captains quarters on the lake in lynn
Property grounds

Captains quarters on the lake in lynn

Captains quarters on the lake in lynn
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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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. If your ideal holiday 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?
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. Homestay BnB Near Downtown Boston: 5 rooms. 9.7 mi (15.7 km) from the city centre. Irving House At Harvard: Situated 5.5 mi (8.8 km) from the heart of Winchester. Enjoy the local cuisine breakfast and snack bar/deli. The College Club of Boston: 12 rooms. 7.6 mi (12.2 km) from the city centre. Enjoy the library and coffee shop. HomeStay - B&B - Near South Boston - JFK-Umass Area: 4 rooms. Located 10.2 mi (16.3 km) from the core of Winchester.
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 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 such as 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 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.