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Search results; Over 1,000 homes in Winthrop

Guest favourite

Room in Winthrop

Private Room ,Hyde Away-upstairs

1 bedroom, 2 beds, 1 bathroom

4–9 Jul

$868 SGD for 5 nights

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4.87 out of 5 average rating, 39 reviews

Top guest favourite

Home in Monmouth

The Cottage at Red Top - Cozy Lakeside Year-Round

2 bedrooms, 3 beds

30 Aug – 4 Sept

$2,170 SGD for 5 nights

5.0 out of 5 average rating, 55 reviews

Guest favourite

Home in Winthrop

Luxury Timber Frame Home | On the Water

4 bedrooms, 7 beds

2–7 Sept

$7,548 SGD for 5 nights

4.97 out of 5 average rating, 58 reviews

Guest favourite

Flat in Winthrop

Jill's Place!

2 beds

11–16 Jul

$1,278 SGD for 5 nights

4.95 out of 5 average rating, 83 reviews

Guest favourite

Cabin in Winthrop

Cozy cabin in a very fun and convenient location.

1 bedroom, 1 bed

4–11 Jul

$1,987 SGD for 7 nights

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Winthrop

Lake house on Annabessacook

3 bedrooms, 5 beds

6–11 Sept

$2,208 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Top guest favourite

Room in Winthrop

Private Room ,Piano Room

1 queen bed

4–9 Jul

$792 SGD for 5 nights

4.96 out of 5 average rating, 54 reviews

Guest favourite

Home in Monmouth

Spacious Lakeside Comfort - Fall/Winter Wonderland

3 bedrooms, 4 beds

25–30 Aug

$3,159 SGD for 5 nights

4.91 out of 5 average rating, 76 reviews

Top guest favourite

Home in Winthrop

Sandy Beach on Cobbosseecontee Lake!

3 bedrooms, 4 beds

2–9 Sept

$2,931 SGD for 7 nights

4.93 out of 5 average rating, 14 reviews

Guest favourite

Cabin in Winthrop

Quaint & cozy cabin in beautiful wooded setting

1 bedroom, 2 beds

16–21 Aug

4.97 out of 5 average rating, 92 reviews

Home in Winthrop

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

2 bedrooms, 3 beds

28 Aug – 3 Sept

4.65 out of 5 average rating, 17 reviews

Top guest favourite

Flat in Winthrop

A little piece of heaven

1 bedroom, 1 king bed

18–23 Sept

$1,066 SGD for 5 nights

4.98 out of 5 average rating, 120 reviews

Guest favourite

Cottage in Winthrop

Cozy Keyes Cottage | Lakefront • Dock • Kayaks

2 bedrooms, 3 beds

18–23 Jul

4.98 out of 5 average rating, 44 reviews

Top guest favourite

Home in Winthrop

Quiet Lakefront Home, Private Dock!

3 bedrooms, 5 beds

26–31 Aug

$3,007 SGD for 5 nights

5.0 out of 5 average rating, 27 reviews

Top guest favourite

Cabin in Winthrop

Lake Cabin in the Trees

3 bedrooms, 3 beds

17–22 Sept

$3,386 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

$3,958 SGD for 6 nights

4.95 out of 5 average rating, 20 reviews

Top guest favourite

Cottage in Winthrop

Little Landing Cottage | Lakefront · Dock · Kayaks

1 bedroom, 2 queen beds

12–17 Jul

5.0 out of 5 average rating, 19 reviews

Home in Winthrop

Historic Lake Cobbossee Cottage

4 bedrooms, 5 double beds

9–14 Aug

$3,387 SGD for 5 nights

Guest favourite

Home in Winthrop

Central downtown & beach area, fish from backyard

3 bedrooms, 6 beds

19–24 Jul

$2,094 SGD for 5 nights

4.76 out of 5 average rating, 46 reviews