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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Winchendon cottages

Exterior

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 £223
includes taxes & fees
5 Jul - 6 Jul
Cottage beside a waterfall
Exterior

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 £414
includes taxes & fees
7 Jul - 8 Jul
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Exterior

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 £383
includes taxes & fees
6 Jul - 7 Jul
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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Top Winchendon Hotel Reviews

Gardner Inn

Gardner Inn

10/10 Excellent
"Very convenient! Clean and quiet place during the night."
Edna 1-night trip
Posted 1 day ago
Gardner Inn

Find out more about Winchendon

Winchendon Cottages information

Number of reviews
64
Accommodation
23 Cottages
Lowest Price
£223
Highest Price
£414

Frequently asked questions

Why book your cottage in Winchendon with Expedia?
We think a getaway should be hassle-free, so if you're seeking cottages in Winchendon at an affordable rate, Expedia delivers. Save money and go for a low-cost option far from the hustle and bustle, or splurge on a 5-star cottage to pamper your favourite people.
How can I find cheap cottages in Winchendon?
With Expedia's user-friendly filter tool, getting your hands on cheap cottages in Winchendon is a breeze. To view accommodation that are friendly on the wallet, fine-tune your search results by star rating, budget and amenities.
What is there to do in Winchendon near my cottage?
After you've unpacked your suitcases, venture out and explore the amazing things Winchendon has to offer. Lake Dennison State Recreation Area is a top attraction to add to your must-do list.