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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Winchendon cottages

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, (34 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is £277
includes taxes & fees
20 May - 21 May
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Property grounds

Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (13 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is £219
includes taxes & fees
22 May - 23 May
Cottage beside a waterfall
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 £209
includes taxes & fees
18 May - 19 May
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Terrace/patio

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (23 reviews)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
United States
Nicole B.
The price is £275
includes taxes & fees
20 May - 21 May
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and 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

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

10/10 Excellent
"The service and room were great. The food was excellent."
Alfredo 11-night trip
Posted 18 hours ago
Doubletree by Hilton Hotel Leominster

Find out more about Winchendon

Winchendon Cottages information

Number of reviews
82
Accommodation
24 Cottages
Lowest Price
£209
Highest Price
£277

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.