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Search results; 371 homes in Winchendon

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Guest favourite
Place to stay in Winchendon
Enjoy your stay in an Antique Home in a Toy Museum
3 bedrooms, 3 beds, 2 private bathrooms
1–6 Oct
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4.9 out of 5 average rating, 105 reviews
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Superhost
Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.79 out of 5 average rating, 363 reviews
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Apartment in Winchendon
Private 1st Floor Apt @ Winchendon Center Town
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.63 out of 5 average rating, 64 reviews
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Superhost
Home in Rindge
Pine and Pond Retreat
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
New place to stay
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Guest favourite
Cabin in Winchendon
The little house on Mirror Pond
2 bedrooms, 2 queen beds, 1.5 bathrooms
21–26 Oct
4.96 out of 5 average rating, 137 reviews
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Guest favourite
Home in Winchendon
Fully Renovated Cottage
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.97 out of 5 average rating, 39 reviews
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Guest favourite
Home in Winchendon
Modern Waterfront Gem w/ Dock on Lake Monomonac
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.88 out of 5 average rating, 33 reviews
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Guest favourite
Home in Rindge
Lakefront Mid-Century Cottage with Sandy Beach
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.83 out of 5 average rating, 6 reviews
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Flat in Fitchburg
Fitchburg hideaway Home
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 4 reviews
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Home in Temple
Comfortable 3 Bedroom House with Full Kitchen
3 bedrooms, 3 queen beds, 1 bathroom
1–6 Oct
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Home in Ashburnham
Walk to Cushing Academy | Sleeps 10
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
New place to stay
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Superhost
Home in Ashburnham
Tranquil Family Friendly Lakefront Retreat
4 bedrooms, 5 beds, 3 bathrooms
12–17 Oct
4.63 out of 5 average rating, 147 reviews
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Top guest favourite
Home in Ashburnham
Escape to the Lake!
3 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 70 reviews
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Guest favourite
Home in New Ipswich
1800s Manor for Celebrations, Reunions & Retreats
9 bedrooms, 14 beds, 4.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Rooms in Hubbardston
Welcome to Plain View Farm!
2 bedrooms, 2 queen beds, 1.5 bathrooms
18–23 Oct
4.97 out of 5 average rating, 33 reviews
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Home in Templeton
Private 3br & basement 3bth near Trail golf & Lake
4 bedrooms, 3 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Winchendon
Lake Monomonac Cottage with Private Beach & Dock
1 bedroom, 1 queen bed, 1 bathroom
1–8 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Mason
Whittier farm house at Barrett Hill Farm
3 bedrooms, 4 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 22 reviews
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Guest favourite
Guest house in Winchendon
Copley’s Guest House on Lake Monomonac
1 bedroom, 2 beds, 1 bathroom
5–10 Oct
4.93 out of 5 average rating, 74 reviews