Hotels in Winchester

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Check prices for these dates

Tonight
Feb 24 - Feb 25
Tomorrow
Feb 25 - Feb 26
This weekend
Feb 28 - Mar 2
Next weekend
Mar 7 - Mar 9

Where to stay in Winchester?

Best Western Plus New Englander
Lobby

Best Western Plus New Englander

2.5 star property
8.2 out of 10, Very Good, (1004)
The price is P6,467
P7,223 total
includes taxes & fees
Mar 2 - Mar 3
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 featuring a sporting event and night scenes as well as a large group of people

Fenway Park

Why not catch an event at Fenway Park, a major stadium in Fenway–Kenmore. If you think Fenway Park is cool, you also might like TD Garden and Agganis Arena, both located nearby.

See properties in Fenway Park
Fenway Park

Learn more about Winchester

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

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Frequently asked questions

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.