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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
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Aug
Top guest favourite
Home in Winthrop
Lake house on Annabessacook
4.94 out of 5 average rating, 18 reviews, 3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
Guest favourite
Cabin in Winthrop
Cottage on Cobbosseecontee!
4.78 out of 5 average rating, 9 reviews, 3 bedrooms, 5 beds, 1 bathroom
1–8 Aug
Guest favourite
Flat in Winthrop
Jill's Place!
4.95 out of 5 average rating, 87 reviews, 2 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
Guest favourite
Cabin in Winthrop
Quaint & cozy cabin in beautiful wooded setting
4.97 out of 5 average rating, 92 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Monmouth
Spacious Lakeside Comfort - Fall/Winter Wonderland
4.91 out of 5 average rating, 78 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
Guest suite in Winthrop
Private Suite in Central Maine
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Winthrop
A little piece of heaven
4.98 out of 5 average rating, 122 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Sept
Guest favourite
Home in Winthrop
July 7-14 Available: Large Porches & Living Space!
4.95 out of 5 average rating, 20 reviews, 5 bedrooms, 7 beds, 2.5 bathrooms
28 Sept – 4 Oct
Top guest favourite
Cottage in Winthrop
Cobbossee Lake cottage with dock
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
14–19 Aug
Home in Winthrop
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
4.67 out of 5 average rating, 18 reviews, 2 bedrooms, 3 beds, 1 bathroom
25 Sept – 1 Oct
Top guest favourite
Home in Winthrop
Quiet Lakefront Home, Private Dock!
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 5 beds, 1 bathroom
26–31 Aug
Top guest favourite
Home in Winthrop
Sandy Beach on Cobbosseecontee Lake!
4.93 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
Home in Winthrop
Lake Front Cozy/Quiet 2 BR Home
4.6 out of 5 average rating, 10 reviews, 2 bedrooms, 2 bathrooms
1–8 Jan
Top guest favourite
Room in Winthrop
Private Room ,Piano Room
4.96 out of 5 average rating, 55 reviews, 1 queen bed, 1 bathroom
1–6 Aug
Top guest favourite
Cabin in Winthrop
Lake Cabin in the Trees
4.98 out of 5 average rating, 65 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Sept
Top guest favourite
Home in Monmouth
The Cottage at Red Top - Cozy Lakeside Year-Round
5.0 out of 5 average rating, 56 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Home in Winthrop
Cobbossee Cottage Lakefront•Private Dock•Fire Pit
3 bedrooms, 5 beds, 1.5 bathrooms
5–10 Sept