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Search results; 354 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
1–6 Aug
,
4.93 out of 5 average rating, 102 reviews
Superhost
Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
4.8 out of 5 average rating, 343 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Superhost
Home in Winchendon
Lake Monomonac Cottage with Private Beach & Dock
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Aug
Top guest favourite
Cabin in Winchendon
The little house on Mirror Pond
4.96 out of 5 average rating, 126 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
Top guest favourite
Home in Winchendon
Fully Renovated Cottage
5.0 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Guest favourite
Home in Winchendon
Modern Waterfront Gem w/ Dock on Lake Monomonac
4.87 out of 5 average rating, 30 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
Top guest favourite
Flat in New Salem
New England Escape
5.0 out of 5 average rating, 71 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Home in Jaffrey
John's Mountain Hideaway
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 2 bathrooms
2–7 Aug
Guest favourite
Cottage in Orange
The Film Shack: A Sweetwater Stay
4.91 out of 5 average rating, 149 reviews, 5 bedrooms, 6 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Home in Jaffrey
Squantum Place
4.98 out of 5 average rating, 50 reviews, 3 bedrooms, 6 beds, 2 bathrooms
6–11 Sept
Guest favourite
Flat in Jaffrey
Schoolhouse No. 1
4.98 out of 5 average rating, 60 reviews, 1 bedroom, 2 beds, 1 bathroom
10–15 Aug
Guest favourite
Flat in Orange
Lakefront Orange Vacation Rental - Pet Friendly!
5.0 out of 5 average rating, 27 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Guest house in Gardner
Eagleview Guesthouse
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Superhost
Cottage in Gardner
Otter's Paradise
4.88 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Guest suite in Hubbardston
In-law Apartment, Full Kitchen, Near Mt Wachusetts
4.98 out of 5 average rating, 214 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Sept
Top guest favourite
Home in Ashburnham
Escape to the Lake!
5.0 out of 5 average rating, 67 reviews, 3 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Winchendon
Casa Tambling Lakefront Escape-Private Sandy Beach
4.88 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
Home in Templeton
Private 3BR Home & bsmt Near Golf, Trails & Shops
New place to stay, 4 bedrooms, 5 beds, 3.5 bathrooms
18–23 Aug
Top guest favourite
Bed and breakfast in Rindge
Rindge Glass Flower Rm1 PvtRoom, PvtBath, King Bed
4.99 out of 5 average rating, 181 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug