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Search results; Over 1,000 homes in Winthrop

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Top guest favourite

Cabin in Winthrop

Lake Cabin in the Trees

3 bedrooms, 3 beds, 2.5 private bathrooms

18–23 Oct

$2,294 SGD for 5 nights

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4.97 out of 5 average rating, 68 reviews

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Guest favourite

Home in Winthrop

Lake house on Annabessacook

3 bedrooms, 5 beds, 2 bathrooms

11–16 Oct

$1,856 SGD for 5 nights

4.96 out of 5 average rating, 24 reviews

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Guest favourite

Home in Winthrop

Journey's End on Maranacook

5 bedrooms, 6 beds, 2.5 bathrooms

13–20 Jun

$4,864 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

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Guest favourite

Home in Winthrop

July 7-14 Available: Large Porches & Living Space!

5 bedrooms, 7 beds, 2.5 bathrooms

1–6 Oct

$2,912 SGD for 5 nights

4.95 out of 5 average rating, 21 reviews

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Dome in Winthrop

Toad Hollow

2 bedrooms, 2 queen beds, 1 bathroom

12–17 Oct

$1,511 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

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Guest favourite

Home in Winthrop

Serene Lakeside Retreat

2 bedrooms, 3 beds, 2 bathrooms

13–18 Oct

$2,208 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

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Guest favourite

Home in Winthrop

Dock + Kayaks: Annabessacook Lake Retreat!

3 bedrooms, 6 beds, 3 bathrooms

5–10 Oct

$3,520 SGD for 5 nights

4.83 out of 5 average rating, 29 reviews

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Home in Winthrop

Lake Front Cozy/Quiet 2 BR Home

2 bedrooms, 2 bathrooms

6–13 Jun

$3,136 SGD for 7 nights

Free cancellation

4.64 out of 5 average rating, 11 reviews

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Top guest favourite

Home in Winthrop

Quiet Lakefront Home, Fall dates open!

3 bedrooms, 5 beds, 1 bathroom

18–23 Oct

$2,372 SGD for 5 nights

5.0 out of 5 average rating, 30 reviews

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Top guest favourite

Home in Winthrop

Sandy Beach on Cobbosseecontee Lake!

3 bedrooms, 4 beds, 1 bathroom

1–6 Oct

$2,112 SGD for 5 nights

4.94 out of 5 average rating, 17 reviews

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Top guest favourite

Cabin in Winthrop

Quaint & cozy cabin in beautiful wooded setting

1 bedroom, 2 beds, 1 bathroom

1–6 Nov

$958 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 100 reviews

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Guest favourite

Home in Winthrop

Large Private Waterfront Lakehouse in Maine

4 bedrooms, 6 beds, 3 bathrooms

14–19 Oct

$2,256 SGD for 5 nights

5.0 out of 5 average rating, 20 reviews

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Guest favourite

Home in Winthrop

Lakeside Retreat

2 bedrooms, 2 beds, 1 bathroom

18–23 Oct

$1,168 SGD for 5 nights

4.95 out of 5 average rating, 19 reviews

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Top guest favourite

Flat in Winthrop

A little piece of heaven

1 bedroom, 1 king bed, 1 bathroom

5–10 Oct

$1,024 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 123 reviews

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Top guest favourite

Flat in Winthrop

Jill's Place!

2 bedrooms, 3 beds, 1 bathroom

10–15 Oct

$1,120 SGD for 5 nights

4.96 out of 5 average rating, 97 reviews

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Guest favourite

Home in Monmouth

Spacious Lakeside Comfort - Fall/Winter Wonderland

3 bedrooms, 4 beds, 2 bathrooms

1–6 Oct

$3,065 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 84 reviews

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Top guest favourite

Rooms in Winthrop

Winthrop House Circa 1843

2 bedrooms, 4 beds, 1 bathroom

3–8 Oct

$967 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 69 reviews

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Flat in Winthrop

2 Bedroom apartment in duplex farmhouse

2 bedrooms, 2 beds, 1 bathroom

1–6 Oct

$781 SGD for 5 nights

Free cancellation

4.67 out of 5 average rating, 58 reviews

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Cottage in Winthrop

Life on the Lake with Private Dock & Fire Pit!

2 bedrooms, 3 beds, 1 bathroom

31 May – 5 Jun

$2,197 SGD for 5 nights

Free cancellation

4.79 out of 5 average rating, 29 reviews