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Search results; Over 1,000 homes in Winthrop

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Top guest favourite

Home in Winthrop

Lake house on Annabessacook

3 bedrooms, 5 beds, 2 private bathrooms

27 Sept – 2 Oct

$2,179 SGD for 5 nights

,

4.95 out of 5 average rating, 22 reviews

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Top guest favourite

Home in Winthrop

Quiet Lakefront Home, Fall dates open!

3 bedrooms, 5 beds

8–13 Sept

$2,362 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

28 Sept – 3 Oct

$2,404 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

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Guest favourite

Home in Winthrop

Large Private Waterfront Lakehouse in Maine

4 bedrooms, 6 beds

1–6 Sept

5.0 out of 5 average rating, 18 reviews

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Guest favourite

Home in Winthrop

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

5 bedrooms, 7 beds

28 Sept – 4 Oct

$3,907 SGD for 6 nights

4.95 out of 5 average rating, 21 reviews

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Guest favourite

Home in Winthrop

Dock + Kayaks: Annabessacook Lake Retreat!

3 bedrooms, 6 beds

5–10 Oct

$3,505 SGD for 5 nights

Free cancellation

4.82 out of 5 average rating, 28 reviews

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Top guest favourite

Cabin in Winthrop

Lake Cabin in the Trees

3 bedrooms, 3 beds

17–22 Sept

4.98 out of 5 average rating, 65 reviews

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Home in Winthrop

Lake Front Cozy/Quiet 2 BR Home

2 bedrooms

1–8 Jan

$3,123 SGD for 7 nights

Free cancellation

4.6 out of 5 average rating, 10 reviews

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Cabin in Winthrop

Cottage on Cobbosseecontee!

3 bedrooms, 5 beds

9–14 Sept

$2,329 SGD for 5 nights

4.83 out of 5 average rating, 12 reviews

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Top guest favourite

Home in Winthrop

Cobbossee Cottage Lakefront•Private Dock•Fire Pit

3 bedrooms, 5 beds

23–28 Sept

$2,282 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

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Guest favourite

Cabin in Winthrop

Cozy Keyes Cottage | Lakefront • Dock • Kayaks

2 bedrooms, 3 beds

7–12 Sept

$4,103 SGD for 5 nights

4.98 out of 5 average rating, 48 reviews

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Superhost

Cabin in Winthrop

Quaint & cozy cabin in beautiful wooded setting

1 bedroom, 2 beds

27 Sept – 2 Oct

4.97 out of 5 average rating, 95 reviews

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Top guest favourite

Flat in Winthrop

A little piece of heaven

1 bedroom, 1 king bed

18–23 Sept

$1,020 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 122 reviews

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Guest favourite

Cottage in Winthrop

Life on the Lake with Private Dock & Fire Pit!

2 bedrooms, 3 beds

31 May – 5 Jun

$2,188 SGD for 5 nights

Free cancellation

4.79 out of 5 average rating, 29 reviews

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Guest favourite

Flat in Winthrop

Jill's Place!

2 bedrooms, 3 beds

10–15 Oct

$1,116 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 93 reviews

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Guest favourite

Home in Winthrop

Loon's Nest on Wilson Pond

3 bedrooms, 9 beds

9–14 Sept

$2,254 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

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Cabin in Winthrop

Family Lakefront home, private dock and fire pit

5 bedrooms, 7 beds

8–13 Sept

$4,132 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

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Top guest favourite

Room in Winthrop

Private Room ,Piano Room

1 queen bed

1–6 Sept

$782 SGD for 5 nights

4.97 out of 5 average rating, 58 reviews

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Top guest favourite

Home in West Gardiner

Lakefront 4BR Home on Peninsula | Private Dock!

4 bedrooms, 7 beds

6–11 Sept

$2,402 SGD for 5 nights

4.93 out of 5 average rating, 14 reviews