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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

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

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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, (443)
"Know that this is a typical small Boston room. There is no dresser. The microwave is in the hall and there is no parking. However, the shower and the toiletries provided are great! Overall, if you can get past the size of the room this hotel is really nice. Make sure to get coffee and pastries from the French bakery next door. "
The price is AED 632
AED 733 total
includes taxes & fees
9 Mar - 10 Mar
Sonder 907 Main
No. 284 powered by Sonder
Exterior

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (874)
"Very quaint, clean space with amazing access to the Boston area. Right between Newbury and Comm Ave, with lots to eat and enjoy."
The price is AED 643
AED 759 total
includes taxes & fees
6 Mar - 7 Mar
No. 284 powered by Sonder
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, (186)
" alue"
The price is AED 393
AED 654 total
includes taxes & fees
19 Mar - 20 Mar
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 BnB Near Downtown Boston: 5 rooms. 9.7 mi (15.7 km) from the downtown core. HomeStay - B&B - Near South Boston - JFK-Umass Area: 4 rooms. Situated 10.2 mi (16.3 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.