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Search results; Over 1,000 homes in Winthrop

Guest favourite

Flat in Winthrop

Jill's Place!

2 bedrooms, 3 beds, 1 private bathroom

29 Aug – 3 Sept

$1,234 SGD for 5 nights

,

4.96 out of 5 average rating, 90 reviews

Guest favourite

Guest suite in Winthrop

Private Suite in Central Maine

1 bedroom, 1 sofa bed

15–20 Aug

Free cancellation

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Home in Winthrop

Quiet Lakefront Home, Private Dock!

3 bedrooms, 5 beds

8–13 Sept

$2,369 SGD for 5 nights

5.0 out of 5 average rating, 29 reviews

Top guest favourite

Rooms in Winthrop

Winthrop House Circa 1843

2 bedrooms, 4 beds

30 Aug – 4 Sept

$1,131 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 68 reviews

Top guest favourite

Room in Winthrop

Private Room ,Piano Room

1 queen bed

13–18 Aug

$784 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 57 reviews

Top guest favourite

Home in Winthrop

Lake house on Annabessacook

3 bedrooms, 5 beds

22–27 Aug

$2,940 SGD for 5 nights

4.95 out of 5 average rating, 22 reviews

Guest favourite

Home in Winthrop

Large Private Waterfront Lakehouse in Maine

4 bedrooms, 6 beds

13–18 Aug

5.0 out of 5 average rating, 16 reviews

Top guest favourite

Flat in Winthrop

A little piece of heaven

1 bedroom, 1 king bed

18–23 Sept

$1,023 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 122 reviews

Guest favourite

Cabin in Winthrop

Quaint & cozy cabin in beautiful wooded setting

1 bedroom, 2 beds

30 Aug – 4 Sept

$957 SGD for 5 nights

4.97 out of 5 average rating, 92 reviews

Top guest favourite

Home in Winthrop

Sandy Beach on Cobbosseecontee Lake!

3 bedrooms, 4 beds

28 Sept – 3 Oct

$2,412 SGD for 5 nights

4.93 out of 5 average rating, 15 reviews

Guest favourite

Cabin in Winthrop

Cottage on Cobbosseecontee!

3 bedrooms, 5 beds

9–14 Sept

4.8 out of 5 average rating, 10 reviews

Guest favourite

Home in Winthrop

Serene Lakeside Retreat

2 bedrooms, 3 beds

14–19 Sept

$2,601 SGD for 5 nights

5.0 out of 5 average rating, 14 reviews

Top guest favourite

Cabin in Winthrop

Lake Cabin in the Trees

3 bedrooms, 3 beds

17–22 Sept

$3,384 SGD for 5 nights

4.98 out of 5 average rating, 65 reviews

Guest favourite

Home in Winthrop

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

5 bedrooms, 7 beds

28 Sept – 4 Oct

$3,919 SGD for 6 nights

4.95 out of 5 average rating, 21 reviews

Home in Winthrop

Lake Front Cozy/Quiet 2 BR Home

2 bedrooms

1–8 Jan

$3,133 SGD for 7 nights

4.6 out of 5 average rating, 10 reviews

Superhost

Home in Winthrop

Luxury Timber Frame Home | On the Water

4 bedrooms, 7 beds

2–7 Sept

$7,462 SGD for 5 nights

4.9 out of 5 average rating, 62 reviews

Guest favourite

Home in Winthrop

Dock + Kayaks: Annabessacook Lake Retreat!

3 bedrooms, 6 beds

5–10 Oct

$3,517 SGD for 5 nights

4.8 out of 5 average rating, 25 reviews

Guest favourite

Home in Winthrop

Central downtown & beach area, fish from backyard

3 bedrooms, 6 beds

16–21 Aug

$2,074 SGD for 5 nights

4.76 out of 5 average rating, 50 reviews

Top guest favourite

Home in Monmouth

The Cottage at Red Top - Cozy Lakeside Year-Round

2 bedrooms, 3 beds

30 Aug – 4 Sept

$2,094 SGD for 5 nights

5.0 out of 5 average rating, 58 reviews