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Search results; 342 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, 106 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
4.62 out of 5 average rating, 65 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
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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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 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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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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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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Top guest favourite
Home in Ashburnham
Charming carriage house in woods with lake access
3 bedrooms, 7 beds, 1 bathroom
11–16 Oct
4.97 out of 5 average rating, 31 reviews
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Home in Templeton
Private 3br & basement 3bth near Trail golf & Lake
4 bedrooms, 3 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 4 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
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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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Top guest favourite
Bed and breakfast in Rindge
Rindge Glass Flower Rm 2: Pvt Room&Bath Queen Bed
1 bedroom, 1 bed, 1 bathroom
2–7 Nov
4.98 out of 5 average rating, 102 reviews
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Top guest favourite
Home in Jaffrey
Squantum Place
3 bedrooms, 6 beds, 2 bathrooms
1–6 Apr
4.98 out of 5 average rating, 55 reviews
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Guest favourite
Guest suite in Jaffrey
Lucy's Lodge - Host lives onsite in secondary unit
4 bedrooms, 11 beds, 2.5 bathrooms
21–26 Oct
4.93 out of 5 average rating, 30 reviews
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Home in Royalston
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
4.94 out of 5 average rating, 77 reviews
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Top guest favourite
Home in Ashburnham
Lake House with island and boats to cruise on!
3 bedrooms, 4 beds, 1 bathroom
30 Oct – 4 Nov
4.96 out of 5 average rating, 70 reviews