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Search results; 349 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
9–14 Aug
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4.93 out of 5 average rating, 102 reviews
Superhost
Home in Rindge
Lakefront Mid-Century Cottage with Sandy Beach
2 bedrooms, 3 beds, 1 bathroom
13–18 Aug
New place to stay
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, 348 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, 8 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
Top guest favourite
Home in Winchendon
Fully Renovated Cottage
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Chalet in Rindge
Cabin & Sauna on Lake Monomonac
2 bedrooms, 2 queen beds, 1.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 52 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
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
Top guest favourite
Flat in Jaffrey
Schoolhouse No. 1
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
4.97 out of 5 average rating, 61 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, 141 reviews
Top guest favourite
Guest suite in Hubbardston
In-law Apartment, Full Kitchen, Near Mt Wachusetts
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 217 reviews
Home in Templeton
Private 3br & basement 3bth near Trail golf & Lake
4 bedrooms, 3 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Keene
Modern Downtown Escape HotTub Fire Pit Games 12ppl
3 bedrooms, 5 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 206 reviews
Top guest favourite
Home in Jaffrey
Squantum Place
3 bedrooms, 6 beds, 2 bathrooms
6–11 Sept
4.98 out of 5 average rating, 52 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
Guest favourite
Home in Westminster
Wachusett Mountain Get-Away
3 bedrooms, 5 beds, 2.5 bathrooms
12–17 Aug
4.94 out of 5 average rating, 142 reviews
Guest favourite
Cabin in Rindge
Beautiful Lakefront Log Cabin
3 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 135 reviews
Top guest favourite
Guest suite in Jaffrey
Comfy Quarters Suite 1
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.95 out of 5 average rating, 365 reviews