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Search results; Over 1,000 homes in Winthrop

Guest favourite
Room in Winthrop
Private Room ,Hyde Away-upstairs
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
,
4.88 out of 5 average rating, 40 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
Home in Winthrop
Lake Front Cozy/Quiet 2 BR Home
2 bedrooms
1–8 Jan
4.6 out of 5 average rating, 10 reviews
Guest favourite
Home in Winthrop
July 7-14 Available: Large Porches & Living Space!
5 bedrooms, 7 beds
28 Sept – 4 Oct
4.95 out of 5 average rating, 21 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
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
Top guest favourite
Home in Winthrop
Quiet Lakefront Home, Fall dates open!
3 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 30 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
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
Top guest favourite
Flat in Winthrop
A little piece of heaven
1 bedroom, 1 king bed
21–26 Sept
4.98 out of 5 average rating, 122 reviews
Guest favourite
Home in Winthrop
Cobbossee Cottage Lakefront•Private Dock•Fire Pit
3 bedrooms, 5 beds
29 Sept – 4 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Tiny home in Winthrop
Lakefront guest cottage,
1 bedroom, 2 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Winthrop
Large Private Waterfront Lakehouse in Maine
4 bedrooms, 6 beds
14–19 Sept
5.0 out of 5 average rating, 20 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, 98 reviews
Dome in Winthrop
Toad Hollow
2 bedrooms, 2 queen beds
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Monmouth
The Cottage at Red Top - Cozy Lakeside Year-Round
2 bedrooms, 3 beds
17–22 Oct
5.0 out of 5 average rating, 61 reviews
Guest favourite
Cottage in Winthrop
Life on the Lake with Private Dock & Fire Pit!
2 bedrooms, 3 beds
31 May – 5 Jun
4.79 out of 5 average rating, 29 reviews
Home in Winthrop
Historic Lake Cobbossee Cottage
4 bedrooms, 5 double beds
1–6 Nov
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cabin in Winthrop
Cottage on Cobbosseecontee!
3 bedrooms, 5 beds
16–21 Sept
4.83 out of 5 average rating, 12 reviews