We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Winthrop

Top guest favourite

Flat in Winthrop

A little piece of heaven

1 bedroom, 1 bed, 1 private bathroom

18–23 Sept

$1,018 SGD for 5 nights

,

4.98 out of 5 average rating, 122 reviews

Top guest favourite

Home in Winthrop

Lake house on Annabessacook

3 bedrooms, 5 beds

22–27 Aug

4.95 out of 5 average rating, 22 reviews

Guest favourite

Home in Winthrop

Serene Lakeside Retreat

2 bedrooms, 3 beds

14–19 Sept

$2,586 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

Guest favourite

Home in Winthrop

Dock + Kayaks: Annabessacook Lake Retreat!

3 bedrooms, 6 beds

5–10 Oct

$3,497 SGD for 5 nights

4.81 out of 5 average rating, 27 reviews

Guest favourite

Home in Winthrop

Luxury Timber Frame Home | On the Water

4 bedrooms, 7 beds

2–7 Sept

$7,419 SGD for 5 nights

4.9 out of 5 average rating, 63 reviews

Top guest favourite

Home in Winthrop

Quiet Lakefront Home, Private Dock!

3 bedrooms, 5 beds

8–13 Sept

$2,356 SGD for 5 nights

5.0 out of 5 average rating, 29 reviews

Guest favourite

Cabin in Winthrop

Quaint & cozy cabin in beautiful wooded setting

1 bedroom, 2 beds

30 Aug – 4 Sept

4.97 out of 5 average rating, 93 reviews

Guest favourite

Flat in Winthrop

Jill's Place!

2 bedrooms, 3 beds

5–10 Oct

$1,205 SGD for 5 nights

4.96 out of 5 average rating, 91 reviews

Guest favourite

Home in Winthrop

Large Private Waterfront Lakehouse in Maine

4 bedrooms, 6 beds

31 Aug – 5 Sept

$3,653 SGD for 5 nights

5.0 out of 5 average rating, 18 reviews

Guest favourite

Cabin in Winthrop

Cottage on Cobbosseecontee!

3 bedrooms, 5 beds

9–14 Sept

4.82 out of 5 average rating, 11 reviews

Guest favourite

Cottage in Winthrop

Cozy Keyes Cottage | Lakefront • Dock • Kayaks

2 bedrooms, 3 beds

7–12 Sept

$3,331 SGD for 5 nights

4.98 out of 5 average rating, 47 reviews

Top guest favourite

Home in Winthrop

Sandy Beach on Cobbosseecontee Lake!

3 bedrooms, 4 beds

28 Sept – 3 Oct

$2,398 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Top guest favourite

Home in Monmouth

The Cottage at Red Top - Cozy Lakeside Year-Round

2 bedrooms, 3 beds

30 Aug – 4 Sept

$2,096 SGD for 5 nights

5.0 out of 5 average rating, 61 reviews

Guest favourite

Guest suite in Winthrop

Private Suite in Central Maine

1 bedroom, 1 sofa bed

30 Aug – 4 Sept

Free cancellation

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in Winthrop

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

5 bedrooms, 7 beds

28 Sept – 4 Oct

$3,897 SGD for 6 nights

4.95 out of 5 average rating, 21 reviews

Top guest favourite

Cabin in Winthrop

Lake Cabin in the Trees

3 bedrooms, 3 beds

17–22 Sept

$3,382 SGD for 5 nights

4.98 out of 5 average rating, 65 reviews

Top guest favourite

Room in Winthrop

Private Room ,Piano Room

1 queen bed

20–25 Aug

$780 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 58 reviews

Guest favourite

Home in Monmouth

Spacious Lakeside Comfort - Fall/Winter Wonderland

3 bedrooms, 4 beds

25–30 Aug

$3,034 SGD for 5 nights

Free cancellation

4.91 out of 5 average rating, 82 reviews

Home in Winthrop

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

2 bedrooms, 3 beds

25 Sept – 1 Oct

4.67 out of 5 average rating, 18 reviews