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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

$2,222 SGD for 5 nights

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4.97 out of 5 average rating, 67 reviews

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Guest favourite

Home in Winthrop

Lake house on Annabessacook

3 bedrooms, 5 beds, 2 bathrooms

11–16 Oct

4.96 out of 5 average rating, 24 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

$3,047 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 84 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

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

$1,300 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Photo 1 of 29

Guest favourite

Home in Winthrop

Serene Lakeside Retreat

2 bedrooms, 3 beds, 2 bathrooms

13–18 Oct

5.0 out of 5 average rating, 19 reviews

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Guest favourite

Home in Winthrop

Large Private Waterfront Lakehouse in Maine

4 bedrooms, 6 beds, 3 bathrooms

5–10 Oct

$1,982 SGD for 5 nights

5.0 out of 5 average rating, 20 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

Free cancellation

4.98 out of 5 average rating, 123 reviews

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Top guest favourite

Home in Monmouth

The Cottage at Red Top - Cozy Lakeside Year-Round

2 bedrooms, 3 beds, 1 bathroom

17–22 Oct

$2,088 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 61 reviews

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Guest favourite

Home in Winthrop

Dock + Kayaks: Annabessacook Lake Retreat!

3 bedrooms, 6 beds, 3 bathrooms

5–10 Oct

$3,507 SGD for 5 nights

4.83 out of 5 average rating, 29 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

$2,363 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

$2,104 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

$953 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 100 reviews

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Top guest favourite

Rooms in Winthrop

Winthrop House Circa 1843

2 bedrooms, 4 beds, 1 bathroom

3–8 Oct

$957 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 69 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

$4,846 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

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Guest favourite

Home in Winthrop

Lakeside Retreat

2 bedrooms, 2 beds, 1 bathroom

18–23 Oct

$1,164 SGD for 5 nights

4.95 out of 5 average rating, 19 reviews

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Home in Winthrop

Lake Front Cozy/Quiet 2 BR Home

2 bedrooms, 2 bathrooms

6–13 Jun

$3,124 SGD for 7 nights

Free cancellation

4.64 out of 5 average rating, 11 reviews

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Top guest favourite

Flat in Winthrop

Jill's Place!

2 bedrooms, 3 beds, 1 bathroom

10–15 Oct

$1,116 SGD for 5 nights

4.96 out of 5 average rating, 97 reviews

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Flat in Winthrop

2 Bedroom apartment in duplex farmhouse

2 bedrooms, 2 beds, 1 bathroom

1–6 Oct

$778 SGD for 5 nights

Free cancellation

4.67 out of 5 average rating, 58 reviews