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Search results; 378 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, 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
20–25 Sept
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
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, 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
21–26 Sept
4.88 out of 5 average rating, 32 reviews
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Superhost
Home in Ashburnham
Tranquil Family Friendly Lakefront Retreat
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
4.63 out of 5 average rating, 147 reviews
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Guest favourite
Home in Rindge
Lakefront Mid-Century Cottage with Sandy Beach
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.83 out of 5 average rating, 6 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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Home in Ashburnham
Walk to Cushing Academy | Sleeps 10
4 bedrooms, 4 beds, 3.5 bathrooms
20–25 Sept
New place to stay
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Guest favourite
Home in Rindge
Wake Up on the Water | Private Beach & Dock
3 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 58 reviews
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Guest favourite
Home in Winchendon
Amazing Lakefront Home with Pool- Tatum's Place
5 bedrooms, 7 beds, 4 bathrooms
12–17 Mar
4.89 out of 5 average rating, 54 reviews
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Guest favourite
Home in New Ipswich
1800s Manor for Celebrations, Reunions & Retreats
9 bedrooms, 14 beds, 4.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 6 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
21–26 Sept
4.97 out of 5 average rating, 30 reviews
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Top guest favourite
Home in Jaffrey
Squantum Place
3 bedrooms, 6 beds, 2 bathrooms
21–26 Sept
4.98 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Rindge
Lakefront Serenity | Dock, Small Beach & Views
4 bedrooms, 8 beds, 2 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 14 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
20–25 Sept
4.98 out of 5 average rating, 102 reviews