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Search results; Over 1,000 homes in Winthrop

Home in Winthrop
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
2 bedrooms, 3 beds, 1 bathroom
25 Sept – 1 Oct
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4.65 out of 5 average rating, 17 reviews
Guest favourite
Home in Winthrop
Luxury Timber Frame Home | On the Water
4 bedrooms, 7 beds, 3.5 bathrooms
2–7 Sept
4.97 out of 5 average rating, 58 reviews
Guest favourite
Flat in Winthrop
Jill's Place!
2 beds, No bathroom
12–17 Jul
4.95 out of 5 average rating, 83 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, 55 reviews
Guest favourite
Cabin in Winthrop
Quaint & cozy cabin in beautiful wooded setting
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 92 reviews
Guest favourite
Home in Winthrop
Lake house on Annabessacook
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.94 out of 5 average rating, 16 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, 76 reviews
Top guest favourite
Home in Winthrop
Sandy Beach on Cobbosseecontee Lake!
3 bedrooms, 4 beds, 1 bathroom
2–9 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Room in Winthrop
Private Room ,Piano Room
1 queen bed, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 54 reviews
Guest favourite
Cabin in Winthrop
Cozy cabin in a very fun and convenient location.
1 bedroom, 1 bed, 1 bathroom
11–18 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Cottage in Winthrop
Cozy Keyes Cottage | Lakefront • Dock • Kayaks
2 bedrooms, 3 beds, 1 bathroom
18–23 Jul
4.98 out of 5 average rating, 44 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, 120 reviews
Top guest favourite
Home in Winthrop
Quiet Lakefront Home, Private Dock!
3 bedrooms, 5 beds, 1 bathroom
26–31 Aug
5.0 out of 5 average rating, 27 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, 20 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
Top guest favourite
Cabin in Readfield
Pet-Friendly Lakefront A-Frame
3 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 75 reviews
Home in Winthrop
Historic Lake Cobbossee Cottage
4 bedrooms, 5 double beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Winthrop
Central downtown & beach area, fish from backyard
3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
4.76 out of 5 average rating, 46 reviews
Guest favourite
Cottage in Winthrop
Cobbossee Lake cottage with dock
2 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 13 reviews