Hotels in Winchester

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Check prices for these dates

Tonight
Jun 2 - Jun 3
Tomorrow
Jun 3 - Jun 4
This weekend
Jun 6 - Jun 8
Next weekend
Jun 13 - Jun 15

Where to stay in Winchester?

Best Western Plus New Englander
Lobby

Best Western Plus New Englander

2.5 star property
8.4 out of 10, Very Good, (1001)
The price is ₩210,287
₩234,891 total
includes taxes & fees
Jun 8 - Jun 9
Best Western Plus New Englander
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.

Top landmarks in Winchester

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

Fenway–Kenmore is home to Fenway Park and is a popular place to see in Boston. Boston has other popular activities such as TD Garden.

See properties in Fenway Park
Fenway Park

Learn more about Winchester

Winchester is well-known for its attractions such as Winter Pond and Middlesex Fells Reservation.

See all hotels in Winchester

Frequently asked questions

What accommodations do travelers like in Winchester?
Guests like YOTEL Boston, Four Points by Sheraton Boston Newton and The Dagny Boston.
Can I book a refundable hotel in Winchester?
If you want the flexibility to change your plans to Winchester, most accommodations offer refundable* bookable rates. You can find these properties by searching our site and using the “fully refundable” filter to narrow the results down.
What will the weather in Winchester be like during my trip?
The warmest months in Winchester are usually July and August with an average temp of 69°F. January and February are the chilliest months when the average temp is 33°F. The rainiest months are December and October.
Why should I book my Winchester hotel through Hotels.com?
There are plenty of reasons to book your Winchester travel with us: our free cancellations on selected hotels* gives you the flexibility you’re looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.