Winchendon Travel Guide

Tourist Guide

Cozy Lakefront Cottage

Cozy Lakefront Cottage

Winchendon
Stay at this vacation home in Winchendon. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Paradise Island and Blueberry Island are located ...
9.8/10 Exceptional! (19 reviews)
Spend your time enjoying nature and the outdoors. Do your grocery shopping during the day as the road is winding and dark. Enjoy evenings sitting around the firepit or on the porchswing literally on the water!! Access to canoes and paddles at your leisure. Full kitchen.

Reviewed on 28 Sept 2025

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Cozy Lakefront Cottage
Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

3 out of 5
Winchendon
Stay at this 3-star cottage in Winchendon. Enjoy free parking and air conditioning. Popular attractions Paradise Island and Blueberry Island are located ...
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Modern Waterfront Gem w/ Dock on Lake Monomonac
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Stay at this 3-star business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (1,002 reviews)
Very nice hotel.

Reviewed on 13 Nov 2025

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The Colonial Hotel
See all 208 properties in Winchendon
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.
Cozy Lakefront Cottage

Cozy Lakefront Cottage

Winchendon
Stay at this vacation home in Winchendon. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Paradise Island and Blueberry Island are located ...
9.8/10 Exceptional! (19 reviews)
Spend your time enjoying nature and the outdoors. Do your grocery shopping during the day as the road is winding and dark. Enjoy evenings sitting around the firepit or on the porchswing literally on the water!! Access to canoes and paddles at your leisure. Full kitchen.

Reviewed on 28 Sept 2025

Cozy Lakefront Cottage
Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

3 out of 5
Winchendon
Stay at this 3-star cottage in Winchendon. Enjoy free parking and air conditioning. Popular attractions Paradise Island and Blueberry Island are located ...
Modern Waterfront Gem w/ Dock on Lake Monomonac
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Fitzwilliam
Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Sportsman Pond and Laurel Lake are located nearby.
10/10 Exceptional! (10 reviews)
It was a lovely stay! Lake is beautiful and the house is cozy.

Reviewed on 16 Oct 2025

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
See all properties in Winchendon
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.

Popular places to visit

The Winchendon School

Enjoy the student vibe at The Winchendon School during your visit to Winchendon. While you're in the area, wander around the parks.

The Winchendon School

Lake Dennison State Recreation Area

You can take time to visit Lake Dennison State Recreation Area during your travels to Winchendon. Discover the area's waterfalls and mountain views.

Lake Dennison State Recreation Area

Monument Park

Monument Park is just one of the places to see in Winchendon, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the parks.

Monument Park

Hyde Park

Explore the great outdoors at Hyde Park, a lovely green space in Winchendon. While you're in the area, wander around the parks.

Hyde Park

Wendall P. Clark Memorial

After visiting Wendall P. Clark Memorial, make a plan to see the other sights and activities in Winchendon. While you're in the area, wander around the parks.

Wendall P. Clark Memorial

Militia Training Field

Explore the great outdoors at Militia Training Field, a lovely green space in Winchendon. While you're in the area, wander around the parks.

Militia Training Field