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Search results; Over 1,000 homes in Winthrop

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Top guest favourite
Tiny home in Winthrop
Lakefront guest cottage,
1 bedroom, 2 beds, 1 private bathroom
13–18 Oct
,
5.0 out of 5 average rating, 46 reviews
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Guest favourite
Home in Winthrop
Lake house on Annabessacook
3 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
4.96 out of 5 average rating, 23 reviews
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Dome in Winthrop
Toad Hollow
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 3 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
July 7-14 Available: Large Porches & Living Space!
5 bedrooms, 7 beds, 2.5 bathrooms
1–6 Oct
4.95 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Winthrop
Quiet Lakefront Home, Fall dates open!
3 bedrooms, 5 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 30 reviews
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Top guest favourite
Home in Winthrop
Sandy Beach on Cobbosseecontee Lake!
3 bedrooms, 4 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 16 reviews
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Guest favourite
Home in Winthrop
Large Private Waterfront Lakehouse in Maine
4 bedrooms, 6 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 20 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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Top guest favourite
Cabin in Winthrop
Lake Cabin in the Trees
3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Oct
4.97 out of 5 average rating, 67 reviews
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Top guest favourite
Flat in Winthrop
A little piece of heaven
1 bedroom, 1 king bed, 1 bathroom
5–10 Oct
4.98 out of 5 average rating, 122 reviews
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Home in Winthrop
Lake Front Cozy/Quiet 2 BR Home
2 bedrooms, 2 bathrooms
6–13 Jun
4.64 out of 5 average rating, 11 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
4.96 out of 5 average rating, 99 reviews
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Guest favourite
Home in Winthrop
Lakeside Retreat
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 19 reviews
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Guest favourite
Home in Monmouth
Spacious Lakeside Comfort - Fall/Winter Wonderland
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.92 out of 5 average rating, 84 reviews
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Top guest favourite
Flat in Winthrop
Jill's Place!
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.96 out of 5 average rating, 97 reviews
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Top guest favourite
Rooms in Winthrop
Winthrop House Circa 1843
2 bedrooms, 4 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 69 reviews
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Cottage in Winthrop
Life on the Lake with Private Dock & Fire Pit!
2 bedrooms, 3 beds, 1 bathroom
31 May – 5 Jun
4.79 out of 5 average rating, 29 reviews
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Guest favourite
Home in Manchester
Lakeside retreat on quiet cove on Cobbessee Lake!
5 bedrooms, 9 beds, 2 bathrooms
18–23 Oct
4.84 out of 5 average rating, 115 reviews