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Search results; 344 homes in Winchendon

Guest favourite
Guest house in Winchendon
Copley’s Guest House on Lake Monomonac
1 bedroom, 2 beds, 1 private bathroom
13–18 Sept
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4.93 out of 5 average rating, 74 reviews
Guest favourite
Place to stay in Winchendon
Enjoy your stay in an Antique Home in a Toy Museum
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.9 out of 5 average rating, 105 reviews
Superhost
Home in Rindge
Pine and Pond Retreat
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
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
4.79 out of 5 average rating, 362 reviews
Apartment in Winchendon
Private 1st Floor Apt @ Winchendon Center Town
2 bedrooms, 2 beds, 1 bathroom
19–24 Oct
4.62 out of 5 average rating, 63 reviews
Guest favourite
Home in Winchendon
Fully Renovated Cottage
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.97 out of 5 average rating, 37 reviews
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
Guest favourite
Home in Rindge
Lakefront Mid-Century Cottage with Sandy Beach
2 bedrooms, 3 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Winchendon
Modern Waterfront Gem w/ Dock on Lake Monomonac
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.88 out of 5 average rating, 32 reviews
Home in Ashburnham
Walk to Cushing Academy | Sleeps 10
4 bedrooms, 4 beds, 3.5 bathrooms
11–16 Sept
New place to stay
Home in Royalston
No. 9
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Sept
New place to stay
Top guest favourite
Home in Ashburnham
Escape to the Lake!
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 70 reviews
Superhost
Home in Ashburnham
Tranquil Family Friendly Lakefront Retreat
4 bedrooms, 5 beds, 3 bathrooms
21–26 Sept
4.62 out of 5 average rating, 146 reviews
Guest favourite
Home in Rindge
Wake Up on the Water | Private Beach & Dock
3 bedrooms, 7 beds, 2 bathrooms
11–16 Sept
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Home in Mason
Whittier farm house at Barrett Hill Farm
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Ashburnham
Charming carriage house in woods with lake access
3 bedrooms, 7 beds, 1 bathroom
12–17 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in Winchendon
Top 10 VRBO Copley's Lakefront Cottage+Guesthouse
4 bedrooms, 9 beds, 4 bathrooms
28 Sept – 3 Oct
4.91 out of 5 average rating, 45 reviews
Top guest favourite
Cottage in Westminster
Cottage @ Partridge Pond
3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Oct
4.99 out of 5 average rating, 95 reviews
Guest favourite
Home in Winchendon
Lake Monomonac Cottage with Private Beach & Dock
1 bedroom, 1 queen bed, 1 bathroom
19–26 Sept
5.0 out of 5 average rating, 15 reviews