A hilly landscape with a tower on top, dense forest, and a cloudy sky.

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Our top choices for Winchendon cottages

Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (15 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is AU$417
includes taxes & fees
5 July - 6 July
Cottage beside a waterfall

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Westminster
9.6 out of 10, Exceptional, (37 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is AU$809
includes taxes & fees
8 July - 9 July
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (12 reviews)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
The price is AU$738
includes taxes & fees
6 July - 7 July
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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.
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Frequently asked questions

What is there to do in Winchendon near my cottage?
The ultimate travel accessory is a well-thought-out travel plan. Doanes Falls is a good place to kick-start your exploration of Winchendon.