Photo by Donny Campos

Hotels in Winchester

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
May 10 - May 11
Tomorrow
May 11 - May 12
Next weekend
May 16 - May 18
In two weeks
May 23 - May 25

Where to stay in Winchester?

Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (152)
$215 nightly
The price is $227
May 12 - May 13
Total includes taxes and fees
Centennial House
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

New England Sweetwater Farm & Distillery

New England Sweetwater Farm & Distillery is in the heart of Winchester, so why not stop by during your stay.

See properties in New England Sweetwater Farm & Distillery
New England Sweetwater Farm & Distillery

Learn more about Winchester

Winchester is well-known for its attractions such as New England Sweetwater Farm & Distillery and Loring Field. The city has something for everyone including sights like Birch Point and Pisgah State Park within a scenic setting.

See all hotels in Winchester
The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, New Hampshire, an unincorporated village of Winchester.
Photo by Donny Campos
Open Photo by Donny Campos
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
Sign in or join for free

Frequently asked questions

What hotels do travelers like in Winchester?
Guests like Beautiful lake side get away, quiet, and peaceful..
Can I book refundable hotels in Winchester?
If you need the flexibility to change your travel plans to Winchester, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the “fully refundable” filter to narrow down the results.
What will the weather in Winchester be like during my vacation?
July and August are typically the warmest months in Winchester when the average temp is 67°F. January and February are the coldest months when the average temperature is 28°F. October and July are the months with the most rain.
Why should I book my Winchester hotel through Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels* gives you flexibility, 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.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

https://www.hotels.com/lp/b/deals