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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchendon cottages

Exterior

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)
"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 CA $245
CA $389 total
includes taxes & fees
Sep 21 - Sep 22
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

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 CA $273
CA $551 total
includes taxes & fees
Oct 14 - Oct 15
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Property grounds

3. Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (21 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 CA $224
CA $405 total
includes taxes & fees
Sep 23 - Sep 24
Cottage beside a waterfall
Exterior

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 CA $224
CA $629 total
includes taxes & fees
Sep 22 - Sep 23
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Exterior

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 CA $294
CA $443 total
includes taxes & fees
Sep 22 - Sep 23
Cozy Tiny House on Main Street. Fully Renovated.
House (3 Bedrooms) | Interior

6. Serene & Sleek Family Retreat w/ Office in Shirley

Serene & Sleek Family Retreat w/ Office in Shirley
3.0 star property
Shirley
The price is CA $424
CA $900 total
includes taxes & fees
Sep 24 - Sep 25
Serene & Sleek Family Retreat w/ Office in Shirley
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

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

10/10 Excellent
"Very convenient with excellent breakfast options. Love being in the old, remodeled building in the town square. Friendly check in staff."
Caroline 2-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott Keene Downtown

Find out more about Winchendon

Winchendon Cottages information

Number of reviews
106
Accommodation
24 Cottages
Lowest Price
CA $389
Highest Price
CA $900

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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.

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