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

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
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 $107
$178 total
includes taxes & fees
Jun 17 - Jun 18
Temple Place Suites
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 $231
$391 total
includes taxes & fees
Jun 16 - Jun 17
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.

Winchester B&B information

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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: Irving House At Harvard: 5.5 mi (8.8 km) from the heart of Winchester. Enjoy the local cuisine breakfast and deli. The College Club of Boston: 12 rooms. 7.6 mi (12.2 km) from the downtown core. Enjoy the unique décor and library. The Salem Inn: Situated 13 mi (21 km) from the heart of Winchester. Enjoy the free cooked breakfast and unique décor. Château sur Mer Bed & Breakfast: 3 rooms. Located 9.2 mi (14.9 km) from the core of Winchester.
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.

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