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Search results; Over 1,000 homes in Winthrop

Guest favourite
Cottage in Winthrop
Little Landing Cottage | Lakefront · Dock · Kayaks
1 bedroom, 2 beds, 1 private bathroom
30 Jun – 5 Jul
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5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Winthrop
Lake house on Annabessacook
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Winthrop
Quiet Lakefront Home, Fall dates open!
3 bedrooms, 5 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 30 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, 15 reviews
Top guest favourite
Home in Winthrop
Sandy Beach on Cobbosseecontee Lake!
3 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Winthrop
Large Private Waterfront Lakehouse in Maine
4 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
5.0 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
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 Winthrop
Dock + Kayaks: Annabessacook Lake Retreat!
3 bedrooms, 6 beds, 3 bathrooms
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, 2.5 bathrooms
17–22 Sept
4.98 out of 5 average rating, 65 reviews
Guest favourite
Cabin in Winthrop
Cottage on Cobbosseecontee!
3 bedrooms, 5 beds, 1 bathroom
9–14 Sept
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Home in Winthrop
Cobbossee Cottage Lakefront•Private Dock•Fire Pit
3 bedrooms, 5 beds, 1.5 bathrooms
23–28 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Winthrop
Luxury Timber Frame Home | On the Water
4 bedrooms, 7 beds, 3.5 bathrooms
2–7 Sept
4.89 out of 5 average rating, 65 reviews
Top guest favourite
Cabin in Winthrop
Quaint & cozy cabin in beautiful wooded setting
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 95 reviews
Guest favourite
Cabin in Winthrop
Cozy Keyes Cottage | Lakefront • Dock • Kayaks
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 47 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
Home in Winthrop
Loon's Nest on Wilson Pond
3 bedrooms, 9 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Cottage in Winthrop
Life on the Lake with Private Dock & Fire Pit!
2 bedrooms, 3 beds, 1 bathroom
31 May – 5 Jun
4.79 out of 5 average rating, 29 reviews
Top guest favourite
Cottage in Winthrop
Cobbossee Lake cottage with dock
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 15 reviews