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Search results; Over 1,000 homes in Winthrop

Guest favourite
Cottage in Winthrop
Cozy Keyes Cottage | Lakefront • Dock • Kayaks
2 bedrooms, 3 beds, 1 private bathroom
19–24 Aug
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4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Winthrop
Large Private Waterfront Lakehouse in Maine
4 bedrooms, 6 beds
3–8 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Winthrop
Lake house on Annabessacook
3 bedrooms, 5 beds
22–27 Aug
4.94 out of 5 average rating, 18 reviews
Guest favourite
Flat in Winthrop
Jill's Place!
2 bedrooms, 3 beds
29 Aug – 3 Sept
4.95 out of 5 average rating, 87 reviews
Top guest favourite
Home in Monmouth
Spacious Lakeside Comfort - Fall/Winter Wonderland
3 bedrooms, 4 beds
25–30 Aug
4.91 out of 5 average rating, 78 reviews
Guest favourite
Cabin in Winthrop
Cottage on Cobbosseecontee!
3 bedrooms, 5 beds
1–8 Aug
4.78 out of 5 average rating, 9 reviews
Guest favourite
Cabin in Winthrop
Quaint & cozy cabin in beautiful wooded setting
1 bedroom, 2 beds
16–21 Aug
4.97 out of 5 average rating, 92 reviews
Guest suite in Winthrop
Private Suite in Central Maine
1 bedroom, 1 sofa bed
1–6 Aug
5.0 out of 5 average rating, 4 reviews
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
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, 20 reviews
Top guest favourite
Cottage in Winthrop
Cobbossee Lake cottage with dock
2 bedrooms, 3 beds
14–19 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Room in Winthrop
Private Room ,Piano Room
1 queen bed
1–6 Aug
4.96 out of 5 average rating, 54 reviews
Home in Winthrop
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
2 bedrooms, 3 beds
25 Sept – 1 Oct
4.67 out of 5 average rating, 18 reviews
Top guest favourite
Home in Winthrop
Quiet Lakefront Home, Private Dock!
3 bedrooms, 5 beds
26–31 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Monmouth
The Cottage at Red Top - Cozy Lakeside Year-Round
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Rooms in Winthrop
Winthrop House Circa 1843
2 bedrooms, 4 beds
1–6 Aug
5.0 out of 5 average rating, 66 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, 65 reviews
Top guest favourite
Home in Winthrop
Sandy Beach on Cobbosseecontee Lake!
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.93 out of 5 average rating, 15 reviews
Home in Winthrop
Cobbossee Cottage Lakefront•Private Dock•Fire Pit
3 bedrooms, 5 beds
5–10 Sept