Hotels in Winchendon

your current months are December, 2024 and January, 2025.
December 2024
January 2025

Find and book your perfect stay

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

Where to stay in Winchendon?

On a rooftop patio, a person leans back in a lounge chair while reading a magazine. Skyscrapers are visible in the distance.

Black Friday: Members save 30%+

One Key™ members save 30%+ on select hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
Unlock Black Friday deals

Top landmarks in Winchendon

The Winchendon School

Explore the campus of The Winchendon School as part of your travels around Winchendon. While you're in the area, wander around the parks.

See properties
The Winchendon School

Frequently asked questions

What accommodations do travelers recommend in Winchendon?
Guests like VRBO Top 10 of 2024!- Copley’s Lakefront Cottage on Lake Monomonac, Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum’s Place and Cozy Lakefront Cottage.
Can I book a refundable hotel in Winchendon?
If you’re looking for the flexibility to change your travel plans to Winchendon, most accommodations provide refundable* bookable rates. You can see these accommodations by searching our site and using the “fully refundable” filter to narrow the results down.
Where can I stay in Winchendon if I want a vacation home instead of a traditional hotel?
Browse 5 vacation homes on our site.
What will the weather in Winchendon be like during my vacation?
The warmest months in Winchendon are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 28°F. The rainiest months are July and October.
Why should I book my Winchendon hotel through Hotels.com?
There are plenty of reasons to book your Winchendon 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.