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Search results; 365 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
27 Sept – 2 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
27 Sept – 2 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
17–22 Sept
New place to stay
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Apartment in Winchendon
Private 1st Floor Apt @ Winchendon Center Town
2 bedrooms, 2 beds
11–16 Oct
4.63 out of 5 average rating, 64 reviews
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Guest favourite
Cabin in Winchendon
The little house on Mirror Pond
2 bedrooms, 2 queen beds
20–25 Sept
4.96 out of 5 average rating, 136 reviews
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Guest favourite
Home in Winchendon
Fully Renovated Cottage
2 bedrooms, 2 beds
26–31 Oct
4.97 out of 5 average rating, 39 reviews
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Superhost
Home in Ashburnham
Tranquil Family Friendly Lakefront Retreat
4 bedrooms, 5 beds
24–29 Sept
4.63 out of 5 average rating, 147 reviews
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Home in Ashburnham
Loon song
1 bedroom, 2 beds
19–24 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Ashburnham
Escape to the Lake!
3 bedrooms, 5 beds
19–24 Oct
5.0 out of 5 average rating, 70 reviews
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Guest favourite
Home in Winchendon
Lake Monomonac Cottage with Private Beach & Dock
1 bedroom, 1 queen bed
26 Sept – 3 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Rindge
Lakefront Serenity | Dock, Small Beach & Views
4 bedrooms, 8 beds
24–29 Sept
4.93 out of 5 average rating, 14 reviews
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Guest favourite
Home in Rindge
Lakefront Mid-Century Cottage with Sandy Beach
2 bedrooms, 3 beds
17–22 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Cabin in Rindge
Lakefront 3BR Log Cabin w/ Dock & Fire Pit
3 bedrooms, 6 beds
23–28 Oct
4.94 out of 5 average rating, 134 reviews
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Guest favourite
Home in Rindge
Wake Up on the Water | Private Beach & Dock
3 bedrooms, 7 beds
17–22 Sept
4.95 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Ashburnham
The Nutty Bird Lakehouse
2 bedrooms, 4 beds
24–29 Oct
5.0 out of 5 average rating, 39 reviews
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Top guest favourite
Cottage in Westminster
Cottage @ Partridge Pond
3 bedrooms, 4 beds
20–25 Oct
4.99 out of 5 average rating, 96 reviews
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Top guest favourite
Cottage in Ashburnham
Cottage with private beach and boats to cruise in
2 bedrooms, 4 beds
4–9 Oct
4.96 out of 5 average rating, 67 reviews
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Top guest favourite
Home in Jaffrey
Willow Falls Home ~Hot tub & Waterfront
3 bedrooms, 3 beds
21–26 Sept
4.98 out of 5 average rating, 108 reviews
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Guest favourite
Home in Winchendon
Modern Waterfront Gem w/ Dock on Lake Monomonac
2 bedrooms, 3 beds
20–25 Sept
4.88 out of 5 average rating, 32 reviews