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Search results; Over 1,000 homes in Winthrop

Top guest favourite

Cabin in Winthrop

Quaint & cozy cabin in beautiful wooded setting

1 bedroom, 2 beds, 1 private bathroom

18–23 Oct

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4.97 out of 5 average rating, 96 reviews

Guest favourite

Home in Winthrop

Lake house on Annabessacook

3 bedrooms, 5 beds, 2 bathrooms

27 Sept – 2 Oct

$2,166 SGD for 5 nights

4.95 out of 5 average rating, 22 reviews

Guest favourite

Home in Winthrop

Journey's End on Maranacook

5 bedrooms, 6 beds, 2.5 bathrooms

12–19 May

$4,891 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Winthrop

Sandy Beach on Cobbosseecontee Lake!

3 bedrooms, 4 beds, 1 bathroom

28 Sept – 3 Oct

$2,390 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Top guest favourite

Home in Winthrop

Quiet Lakefront Home, Fall dates open!

3 bedrooms, 5 beds, 1 bathroom

8–13 Sept

$2,580 SGD for 5 nights

5.0 out of 5 average rating, 30 reviews

Home in Winthrop

Lake Front Cozy/Quiet 2 BR Home

2 bedrooms, 2 bathrooms

1–8 Jan

$3,104 SGD for 7 nights

Free cancellation

4.6 out of 5 average rating, 10 reviews

Guest favourite

Home in Winthrop

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

5 bedrooms, 7 beds, 2.5 bathrooms

4–9 Sept

$3,435 SGD for 5 nights

4.95 out of 5 average rating, 21 reviews

Guest favourite

Home in Winthrop

Serene Lakeside Retreat

2 bedrooms, 3 beds, 2 bathrooms

14–19 Sept

$2,576 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Dome in Winthrop

Toad Hollow

2 bedrooms, 2 queen beds, 1 bathroom

13–18 Sept

$1,430 SGD for 5 nights

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

Guest favourite

Home in Winthrop

Dock + Kayaks: Annabessacook Lake Retreat!

3 bedrooms, 6 beds, 3 bathrooms

5–10 Oct

$3,484 SGD for 5 nights

4.82 out of 5 average rating, 28 reviews

Guest favourite

Home in Winthrop

Cobbossee Cottage Lakefront•Private Dock•Fire Pit

3 bedrooms, 5 beds, 1.5 bathrooms

23–28 Sept

$2,268 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Flat in Winthrop

A little piece of heaven

1 bedroom, 1 king bed, 1 bathroom

18–23 Sept

$1,014 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 122 reviews

Guest favourite

Cabin in Winthrop

Cottage on Cobbosseecontee!

3 bedrooms, 5 beds, 1 bathroom

9–14 Sept

$2,255 SGD for 5 nights

4.83 out of 5 average rating, 12 reviews

Guest favourite

Home in Winthrop

Large Private Waterfront Lakehouse in Maine

4 bedrooms, 6 beds, 3 bathrooms

8–13 Sept

5.0 out of 5 average rating, 18 reviews

Guest favourite

Home in Winthrop

Lakeside Retreat

2 bedrooms, 2 beds, 1 bathroom

18–23 Oct

$1,188 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Top guest favourite

Cabin in Winthrop

Cozy Keyes Cottage | Lakefront • Dock • Kayaks

2 bedrooms, 3 beds, 1 bathroom

7–12 Sept

$3,893 SGD for 5 nights

4.98 out of 5 average rating, 50 reviews

Superhost

Home in Winthrop

Luxury Timber Frame Home | On the Water

4 bedrooms, 7 beds, 3.5 bathrooms

5–10 Sept

$7,430 SGD for 5 nights

4.89 out of 5 average rating, 66 reviews

Guest favourite

Home in Monmouth

Spacious Lakeside Comfort - Fall/Winter Wonderland

3 bedrooms, 4 beds, 2 bathrooms

26 Sept – 1 Oct

Free cancellation

4.92 out of 5 average rating, 84 reviews