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Search results; Over 1,000 homes in Winthrop

Guest favourite
Flat in Winthrop
Jill's Place!
2 bedrooms, 3 beds, 1 private bathroom
29 Aug – 3 Sept
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4.95 out of 5 average rating, 88 reviews
Top guest favourite
Home in Winthrop
Lake house on Annabessacook
3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Winthrop
Serene Lakeside Retreat
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Winthrop
Dock + Kayaks: Annabessacook Lake Retreat!
3 bedrooms, 6 beds, 3 bathrooms
5–10 Oct
4.8 out of 5 average rating, 25 reviews
Guest favourite
Cabin in Winthrop
Cottage on Cobbosseecontee!
3 bedrooms, 5 beds, 1 bathroom
9–14 Sept
4.8 out of 5 average rating, 10 reviews
Top guest favourite
Home in Winthrop
Quiet Lakefront Home, Private Dock!
3 bedrooms, 5 beds, 1 bathroom
4–9 Aug
5.0 out of 5 average rating, 29 reviews
Guest favourite
Cabin in Winthrop
Quaint & cozy cabin in beautiful wooded setting
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.97 out of 5 average rating, 92 reviews
Top guest favourite
Flat in Winthrop
A little piece of heaven
1 bedroom, 1 king bed, 1 bathroom
18–23 Sept
4.98 out of 5 average rating, 122 reviews
Superhost
Home in Winthrop
Luxury Timber Frame Home | On the Water
4 bedrooms, 7 beds, 3.5 bathrooms
2–7 Sept
4.9 out of 5 average rating, 62 reviews
Guest suite in Winthrop
Private Suite in Central Maine
1 bedroom, 1 sofa bed, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Winthrop
Large Private Waterfront Lakehouse in Maine
4 bedrooms, 6 beds, 3 bathrooms
13–18 Aug
5.0 out of 5 average rating, 15 reviews
Home in Winthrop
Lake Front Cozy/Quiet 2 BR Home
2 bedrooms, 2 bathrooms
1–8 Jan
4.6 out of 5 average rating, 10 reviews
Guest favourite
Home in Monmouth
Spacious Lakeside Comfort - Fall/Winter Wonderland
3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
4.91 out of 5 average rating, 79 reviews
Guest favourite
Home in Winthrop
Lakeside Retreat
2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Monmouth
The Cottage at Red Top - Cozy Lakeside Year-Round
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 57 reviews
Guest favourite
Cottage in Winthrop
Cozy Keyes Cottage | Lakefront • Dock • Kayaks
2 bedrooms, 3 beds, 1 bathroom
19–24 Aug
4.98 out of 5 average rating, 46 reviews
Home in Winthrop
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
2 bedrooms, 3 beds, 1 bathroom
25 Sept – 1 Oct
4.67 out of 5 average rating, 18 reviews
Guest favourite
Home in Winthrop
July 7-14 Available: Large Porches & Living Space!
5 bedrooms, 7 beds, 2.5 bathrooms
28 Sept – 4 Oct
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Winthrop
Central downtown & beach area, fish from backyard
3 bedrooms, 6 beds, 1 bathroom
16–21 Aug
4.76 out of 5 average rating, 50 reviews