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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
10–15 Aug
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4.98 out of 5 average rating, 45 reviews
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
6–11 Sept
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
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
Home in Winthrop
Historic Lake Cobbossee Cottage
4 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Home in Winthrop
Quiet Lakefront Home, Private Dock!
5.0 out of 5 average rating, 27 reviews, 3 bedrooms, 5 beds, 1 bathroom
26–31 Aug
Guest favourite
Home in Monmouth
Spacious Lakeside Comfort - Fall/Winter Wonderland
4.91 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
Guest favourite
Flat in Winthrop
Jill's Place!
4.95 out of 5 average rating, 84 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
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
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
Home in Winthrop
Cobbossee Cottage Lakefront•Private Dock•Fire Pit
3 bedrooms, 5 beds, 1.5 bathrooms
31 Aug – 5 Sept
Guest suite in Winthrop
Private Suite in Central Maine
New place to stay, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Cabin in Winthrop
Waterfront Family, pet friendly with firepit/place
5 bedrooms, 5 beds, 2 bathrooms
3–8 Aug
Guest favourite
Cottage in Winthrop
Cobbossee Lake cottage with dock
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
Top guest favourite
Home in Monmouth
The Cottage at Red Top - Cozy Lakeside Year-Round
5.0 out of 5 average rating, 55 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Winthrop
Central downtown & beach area, fish from backyard
4.77 out of 5 average rating, 47 reviews, 3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
Top guest favourite
Rooms in Winthrop
Winthrop House Circa 1843
5.0 out of 5 average rating, 66 reviews, 2 bedrooms, 4 beds, 1 bathroom
27 Jul – 1 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
Guest favourite
Home in Winthrop
Family Homestead 1 hr from beaches! Pet Friendly!
5.0 out of 5 average rating, 12 reviews, 6 bedrooms, 6 beds, 2 bathrooms
1–6 Jan