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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
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
Guest favourite
Flat in Winthrop
Jill's Place!
4.95 out of 5 average rating, 83 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 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 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
Top guest favourite
Flat in Winthrop
A little piece of heaven
4.98 out of 5 average rating, 121 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Sept
Top guest favourite
Room in Winthrop
Private Room ,Piano Room
4.96 out of 5 average rating, 54 reviews, 1 queen bed, 1 bathroom
12–17 Jul
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
Guest favourite
Cabin in Winthrop
Cozy cabin in a very fun and convenient location.
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
11–18 Jul
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
Guest favourite
Home in Winthrop
Serene Lakeside Retreat
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
Guest suite in Winthrop
Private Suite in Central Maine
New place to stay, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Cottage in Winthrop
Little Landing Cottage | Lakefront · Dock · Kayaks
5.0 out of 5 average rating, 19 reviews, 1 bedroom, 2 beds, 1 bathroom
7–12 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
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
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
Cottage in Manchester
Cobbossee Lake Cottage – 3 Bedroom, 2 Bath
4.9 out of 5 average rating, 29 reviews, 3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
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
12–17 Jul
Home in Winthrop
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
4.65 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 1 bathroom
25 Sept – 1 Oct