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Search results; Over 1,000 homes in Winthrop

Top guest favourite
Home in Winthrop
Quiet Lakefront Home, Fall dates open!
3 bedrooms, 5 beds, 1 private bathroom
10–15 Sept
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5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Winthrop
Lake house on Annabessacook
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 23 reviews
Guest favourite
Home in Winthrop
Journey's End on Maranacook
5 bedrooms, 6 beds
12–19 May
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Winthrop
Serene Lakeside Retreat
2 bedrooms, 3 beds
13–18 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cabin in Winthrop
Lake Cabin in the Trees
3 bedrooms, 3 beds
17–22 Sept
4.98 out of 5 average rating, 66 reviews
Home in Winthrop
Lake Front Cozy/Quiet 2 BR Home
2 bedrooms
1–8 Jan
4.6 out of 5 average rating, 10 reviews
Top guest favourite
Home in Winthrop
Sandy Beach on Cobbosseecontee Lake!
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Winthrop
July 7-14 Available: Large Porches & Living Space!
5 bedrooms, 7 beds
10–15 Sept
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Winthrop
Dock + Kayaks: Annabessacook Lake Retreat!
3 bedrooms, 6 beds
5–10 Oct
4.82 out of 5 average rating, 28 reviews
Guest favourite
Home in Winthrop
Large Private Waterfront Lakehouse in Maine
4 bedrooms, 6 beds
10–15 Sept
5.0 out of 5 average rating, 20 reviews
Dome in Winthrop
Toad Hollow
2 bedrooms, 2 queen beds
13–18 Sept
Top guest favourite
Flat in Winthrop
A little piece of heaven
1 bedroom, 1 king bed
18–23 Sept
4.98 out of 5 average rating, 122 reviews
Top guest favourite
Cabin in Winthrop
Quaint & cozy cabin in beautiful wooded setting
1 bedroom, 2 beds
1–6 Nov
4.97 out of 5 average rating, 97 reviews
Guest favourite
Home in Winthrop
Cobbossee Cottage Lakefront•Private Dock•Fire Pit
3 bedrooms, 5 beds
23–28 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Winthrop
Lakeside Retreat
2 bedrooms, 2 beds
18–23 Oct
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Cottage in Winthrop
Cobbossee Lake cottage with dock
2 bedrooms, 3 beds
11–16 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Monmouth
Spacious Lakeside Comfort - Fall/Winter Wonderland
3 bedrooms, 4 beds
26 Sept – 1 Oct
4.92 out of 5 average rating, 84 reviews
Top guest favourite
Flat in Winthrop
Jill's Place!
2 bedrooms, 3 beds
10–15 Oct
4.96 out of 5 average rating, 97 reviews
Top guest favourite
Cabin in Winthrop
Cozy Keyes Cottage | Lakefront • Dock • Kayaks
2 bedrooms, 3 beds
10–15 Sept
4.98 out of 5 average rating, 51 reviews