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Search results; Over 1,000 homes in Winthrop

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Top guest favourite
Cabin in Winthrop
Lake Cabin in the Trees
3 bedrooms, 3 beds, 2.5 private bathrooms
22–27 Sept
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4.98 out of 5 average rating, 66 reviews
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Guest favourite
Home in Winthrop
Lake house on Annabessacook
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 23 reviews
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Guest favourite
Home in Winthrop
July 7-14 Available: Large Porches & Living Space!
5 bedrooms, 7 beds, 2.5 bathrooms
28 Sept – 4 Oct
4.95 out of 5 average rating, 21 reviews
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Guest favourite
Home in Monmouth
Spacious Lakeside Comfort - Fall/Winter Wonderland
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
4.92 out of 5 average rating, 84 reviews
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Dome in Winthrop
Toad Hollow
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Winthrop
Sandy Beach on Cobbosseecontee Lake!
3 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
4.94 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Winthrop
Quiet Lakefront Home, Fall dates open!
3 bedrooms, 5 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 30 reviews
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Top guest favourite
Flat in Winthrop
A little piece of heaven
1 bedroom, 1 king bed, 1 bathroom
21–26 Sept
4.98 out of 5 average rating, 122 reviews
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Top guest favourite
Home in Monmouth
The Cottage at Red Top - Cozy Lakeside Year-Round
2 bedrooms, 3 beds, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 61 reviews
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Guest favourite
Cabin in Winthrop
Family Lakefront home, private dock and fire pit
5 bedrooms, 7 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Winthrop
Dock + Kayaks: Annabessacook Lake Retreat!
3 bedrooms, 6 beds, 3 bathrooms
5–10 Oct
4.82 out of 5 average rating, 28 reviews
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Guest favourite
Home in Winthrop
Serene Lakeside Retreat
2 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Winthrop
Large Private Waterfront Lakehouse in Maine
4 bedrooms, 6 beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Cabin in Winthrop
Cottage on Cobbosseecontee!
3 bedrooms, 5 beds, 1 bathroom
19–24 Sept
4.83 out of 5 average rating, 12 reviews
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Top guest favourite
Cottage in Winthrop
Cobbossee Lake cottage with dock
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Cabin in Winthrop
Quaint & cozy cabin in beautiful wooded setting
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 98 reviews
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Top guest favourite
Rooms in Winthrop
Winthrop House Circa 1843
2 bedrooms, 4 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 69 reviews
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Home in Winthrop
Lake Front Cozy/Quiet 2 BR Home
2 bedrooms, 2 bathrooms
6–13 Jun
4.6 out of 5 average rating, 10 reviews
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Cabin in Readfield
Camp on Maranacook Lake Maine Cabin Mstr renovated
4 bedrooms, 4 beds, 1.5 bathrooms
19–24 Sept
4.79 out of 5 average rating, 19 reviews