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Search results; 345 homes in Winchendon

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Guest favourite
Cabin in Winchendon
The little house on Mirror Pond
2 bedrooms, 2 beds, 1.5 private bathrooms
25–30 Oct
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4.96 out of 5 average rating, 137 reviews
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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 bathrooms
1–6 Oct
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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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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Apartment in Winchendon
Private 1st Floor Apt @ Winchendon Center Town
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.62 out of 5 average rating, 65 reviews
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Cabin in New Ipswich
Bungalow
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.84 out of 5 average rating, 49 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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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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Guest favourite
Home in Winchendon
Fully Renovated Cottage
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 40 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 Winchendon
Top 10 VRBO Copley's Lakefront Cottage+Guesthouse
4 bedrooms, 9 beds, 4 bathrooms
17–22 Oct
4.91 out of 5 average rating, 45 reviews
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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, 148 reviews
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Barn in Ashburnham
Beautiful, Modern Farmhouse, Walk to Cushing!
3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
New place to stay
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Guest favourite
Cabin in Rindge
Cabin & Sauna on Lake Monomonac
2 bedrooms, 2 beds, 1 bathroom
12–17 Oct
4.87 out of 5 average rating, 38 reviews
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Top guest favourite
Cottage in Winchendon
Top 10 of VRBO -Copley's Lakefront Cottage on Lake
3 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
4.98 out of 5 average rating, 59 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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Guest favourite
Home in Rindge
Wake Up on the Water | Private Beach & Dock
3 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
4.95 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Fitzwilliam
Lakefront Home | Near Monadnock
4 bedrooms, 5 beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 21 reviews
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Cabin in Rindge
Secluded Lake Cabin Perfect for Family Fun!
3 bedrooms, 3 queen beds, 1 bathroom
5–10 Oct
4.8 out of 5 average rating, 25 reviews