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Featured Cottages in Winchendon

Our top choices for Winchendon cottages

Historic Home w/ Modern Updates on < 4 Acres
Interior

Historic Home w/ Modern Updates on < 4 Acres

3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
Charming Jaffrey Cottage w/ Deck & Grill!
Interior

Charming Jaffrey Cottage w/ Deck & Grill!

3.0 star property
Charming Jaffrey Cottage w/ Deck & Grill!
Dog-friendly Fitchburg Vacation Rental, Hike & Ski
Interior

Dog-friendly Fitchburg Vacation Rental, Hike & Ski

3.0 star property
Dog-friendly Fitchburg Vacation Rental, Hike & Ski
Modern Waterfront Gem w/ Dock on Lake Monomonac
Interior

Modern Waterfront Gem w/ Dock on Lake Monomonac

3.0 star property
Modern Waterfront Gem w/ Dock on Lake Monomonac
Massachusetts Cabin Rental Near Hiking & Skiing!
Exterior

Massachusetts Cabin Rental Near Hiking & Skiing!

3.0 star property
Massachusetts Cabin Rental Near Hiking & Skiing!
Lakeside Log Cabin w/ Porch in Monadnock Region
Front of property

Lakeside Log Cabin w/ Porch in Monadnock Region

3.0 star property
Lakeside Log Cabin w/ Porch in Monadnock Region
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

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Everything was great."
Christopher 1-night trip
Posted 1 day ago
The Colonial Hotel

Find out more about Winchendon

Find out more about Winchendon

Winchendon Cottages information

Number of reviews
Accommodation
5 Cottages
Lowest Price
Highest Price

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 favorite 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 accommodations 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.

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