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Search results; 346 homes in Winchendon

Top 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
17–22 Aug
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4.93 out of 5 average rating, 103 reviews
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Home in Rindge
Lakefront Mid-Century Cottage with Sandy Beach
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 3 reviews
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Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.79 out of 5 average rating, 354 reviews
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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, 131 reviews
Guest favourite
Home in Winchendon
Fully Renovated Cottage
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
4.97 out of 5 average rating, 35 reviews
Apartment in Winchendon
Private 1st Floor Apt @ Winchendon Center Town
2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
4.61 out of 5 average rating, 62 reviews
Guest favourite
Home in Winchendon
Lake Monomonac Cottage with Private Beach & Dock
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Winchendon
Modern Waterfront Gem w/ Dock on Lake Monomonac
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.87 out of 5 average rating, 31 reviews
Guest favourite
Home in Rindge
Wake Up on the Water | Private Beach & Dock
3 bedrooms, 7 beds, 2 bathrooms
29 Aug – 3 Sept
4.94 out of 5 average rating, 54 reviews
Guest favourite
Guest suite in Ashburnham
The Ginger Bed King and Queen Suite
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.94 out of 5 average rating, 206 reviews
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Home in Rindge
Cottage Cove lakefront home
3 bedrooms, 6 beds, 1 bathroom
21–26 Sept
4.98 out of 5 average rating, 52 reviews
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Flat in New Ipswich
Quiet country apartment in farmland setting.
2 beds, 1 bathroom
23–28 Oct
4.96 out of 5 average rating, 142 reviews
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Cottage in Westminster
Cottage @ Partridge Pond
3 bedrooms, 4 beds, 1.5 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 92 reviews
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Guest house in Peterborough
Dunboy House: A Bright & Playful Retreat
1 bedroom, 2 beds, 1.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Rooms in Jaffrey
Cozy, comfortable Ranch Home
2 bedrooms, 2 beds, 1 bathroom
18–23 Aug
4.82 out of 5 average rating, 88 reviews
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Loft in Peterborough
Peaceful Mill with Waterfall - Home Away From Home
2 bedrooms, 2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 263 reviews
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Cottage in Petersham
Cider House Cottage
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 254 reviews
Top guest favourite
Tiny home in New Ipswich
Quaint, Historic Tiny Home
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 56 reviews
Superhost
Apartment in Troy
The Monadnock Suite
2 bedrooms, 2 queen beds, 1.5 bathrooms
27 Aug – 1 Sept
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