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Search results; 351 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
16–21 Aug
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4.93 out of 5 average rating, 103 reviews
Superhost
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
Superhost
Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.8 out of 5 average rating, 353 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
Top 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, 129 reviews
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Tiny home in New Ipswich
Quaint, Historic Tiny Home
1 bedroom, 1 queen bed, 1 bathroom
15–20 Aug
4.98 out of 5 average rating, 54 reviews
Top guest favourite
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
Top 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
Top guest favourite
Flat in New Ipswich
Quiet country apartment in farmland setting.
2 beds, 1 bathroom
5–10 Oct
4.96 out of 5 average rating, 142 reviews
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Home in Ashburnham
Lake House with island and boats to cruise on!
3 bedrooms, 4 beds, 1 bathroom
27 Oct – 1 Nov
4.96 out of 5 average rating, 70 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, 30 reviews
Top guest favourite
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, 262 reviews
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Cabin in New Salem
Rustic cabin with A/C at historic orchard & cidery
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Ashburnham
Escape to the Lake!
3 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 69 reviews
Top guest favourite
Cottage in Orange
Lake House with view of mountain
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 94 reviews
Top guest favourite
Guest house in New Ipswich
"The Porch" Your cozy home away from home!
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
4.95 out of 5 average rating, 424 reviews
Guest favourite
Home in Gardner
Lodge at Kendall Pond
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.86 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Westminster
Westminster Lodge at Ryan's Ranch
2 bedrooms, 1 queen bed, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Rooms in Hubbardston
Welcome to Plain View Farm!
2 bedrooms, 2 queen beds, 1.5 bathrooms
7–12 Sept
4.97 out of 5 average rating, 32 reviews