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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchendon cottages

A house by a lake with a dock and a boat.

1. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 reviews)
"Jim was a great host very friendly and welcoming, the cabin is in the perfect spot on the lake and we were able to see a fireworks show directly on the dock, thank you !"
United States
clifford t.
The price is £222
includes taxes & fees
20 Oct - 21 Oct
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A red building with a white door and windows, a concrete driveway, and a grassy area with a lake in the background.

2. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is £284
includes taxes & fees
15 Oct - 16 Oct
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A wooden deck with a view of a forested area.

3. Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (22 reviews)
"Unique artist's cottage, curated with great care and humor. Amazing property with an actual waterfall behind the cottage. Nice covered porch to view the scene. Excellent bed."
United States
Patrick B.
The price is £223
includes taxes & fees
28 Oct - 29 Oct
Cottage beside a waterfall
A house with a stone wall and a dock extending into a calm body of water.

4. 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, (42 reviews)
"Very clean and tidy!Tyler was great - even accommodated last minute to add our dogs to the booking!Would definitely stay again!"
United States
Christina C.
The price is £342
includes taxes & fees
18 Oct - 19 Oct
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
A small, single-story building with a front door and a small window.

5. Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
The price is £242
includes taxes & fees
1 Nov - 2 Nov
Cozy Tiny House on Main Street. Fully Renovated.
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

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

10/10 Excellent
"Very nice hotel. Loved the Hot Cocoa Bar they had in lobby. Breakfast had a wide variety of food items. Many places to sit. Everyone very nice."
Nora 1-night trip
Posted 2 hours ago
Hampton Inn & Suites Keene

Find out more about Winchendon

Winchendon Cottages information

Number of reviews
85
Accommodation
24 Cottages
Lowest Price
£222
Highest Price
£342

Frequently asked questions

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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.