Hotels in Winchendon

Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices

Check prices for these dates

Tonight
Jul 8 - Jul 9
Tomorrow
Jul 9 - Jul 10
This weekend
Jul 11 - Jul 13
Next weekend
Jul 18 - Jul 20

Where to stay in Winchendon?

The Maguire House Bed & Breakfast
Building design

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
The price is $275
$275 total
includes taxes & fees
Jul 17 - Jul 18
The Maguire House Bed & Breakfast
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 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 in The Winchendon School
The Winchendon School

Learn more about Winchendon

Winchendon is well-known for its attractions such as Lake Dennison State Recreation Area and Millers River.

See all hotels in Winchendon

Check out reviews of Winchendon hotels guests love

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"My Daughter And I Stayed 3 Days 4th Of July And Loved Pretty Much Everything!! Staff Were Great,Breakfast Wow Awesome, Indoor Pool,Beautiful Gazebo And Other Outdoor Lights!! Our Only Note*Rotate The Mattresses 1Side Of Bed Sinks,The Other Side Firm!! Tyvm 😁 😊 We Will Be Returning Soon!! Maureen 💗 "
Maureen 3-night trip
Posted 2 days ago
Best Western Plus Keene Hotel

Frequently asked questions

What accommodations do travelers recommend in Winchendon?
Guests like Modern Waterfront Gem w/ Dock on Lake Monomonac and The Colonial Hotel.
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.