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Search results; Over 1,000 homes in Long Island

Guest favourite

Home in Long Island

Whole house on a great island in Casco Bay!

3 bedrooms, 4 beds, 2 private bathrooms

7–12 Sept

$4,332 SGD for 5 nights

,

4.99 out of 5 average rating, 76 reviews

Home in Long Island

500Island

4 bedrooms, 5 beds, 2.5 bathrooms

23–30 Aug

$11,009 SGD for 7 nights

Pay $0 today

Free cancellation

New place to stay

Guest favourite

Cottage in Long Island

Picturesque Maine water view Long Island

4 bedrooms, 5 beds, 1 bathroom

27 Sept – 4 Oct

$4,649 SGD for 7 nights

Free cancellation

4.82 out of 5 average rating, 50 reviews

Guest favourite

Cottage in Long Island

A Once in a Lifetime Oceanfront Escape

2 bedrooms, 3 beds, 1 bathroom

1–6 Sept

$6,770 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Home in Long Island

Spacious Long Island Retreat

4 bedrooms, 8 beds, 2 bathrooms

9–14 Sept

$3,159 SGD for 5 nights

Free cancellation

Superhost

Room in Portland

Aerie 2 reg:STHR-007375-2025 Peaks Island, Me

1 bed, 1 bathroom

30 Aug – 4 Sept

$1,169 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Cottage in Portland

Casco-Vista, Island Cottage

3 bedrooms, 3 beds, 1.5 bathrooms

6–11 Sept

$3,192 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 26 reviews

Superhost

Home in Portland

Gull Cottage: A Classic Peaks Island Charmer

3 bedrooms, 4 beds, 1 bathroom

6–13 Sept

Superhost

Home in Freeport

Casco Bay Beachfront Retreat

3 bedrooms, 5 beds, 2 bathrooms

9–14 Sept

$5,106 SGD for 5 nights

Free cancellation

New place to stay

Top guest favourite

Home in Portland

Modern Peaks Island Getaway | Ocean Views + Decks

2 bedrooms, 3 beds, 2 bathrooms

29 Aug – 3 Sept

$4,990 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Cottage in Portland

Captain's Quarters on Peaks Island

1 bedroom, 1 bed, 1 bathroom

1–6 Jan

$2,356 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 40 reviews

Home in Portland

Historic Island Retreat

2 bedrooms, 3 beds, 2 bathrooms

1–6 Nov

$1,900 SGD for 5 nights

Guest favourite

Guest suite in Yarmouth

Ash + Timber | Forest Sauna Suite Near Portland

1 bedroom, 2 beds, 1 bathroom

20–25 Oct

$2,396 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Guest house in Chebeague Island

Wellhouse Cottage, A Peaceful Maine Getaway

1 bedroom, 1 double bed, 1 bathroom

10–15 Sept

$1,343 SGD for 5 nights

Pay $0 today

Free cancellation

Top guest favourite

Cabin in Freeport

Chickadee A-Frame

3 bedrooms, 3 beds, 2 bathrooms

18–23 Oct

$2,582 SGD for 5 nights

Pay $0 today

Free cancellation

4.97 out of 5 average rating, 79 reviews

Home in Westbrook

Cozy Cape in the Brook

2 bedrooms, 3 beds, 1 bathroom

10–15 Aug

$2,136 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Top guest favourite

Home in Cape Elizabeth

Pastoral Tranquil Walk to Trails Dining Shopping

3 bedrooms, 4 beds, 1 bathroom

6–11 Sept

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 34 reviews

Top guest favourite

Flat in Portland

The Yankee Dugout

2 bedrooms, 3 beds, 1 bathroom

30 Aug – 4 Sept

$1,924 SGD for 5 nights

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 193 reviews

Superhost

Home in Harpswell

The Beach Pea - Waterfront cottage, Pet Friendly!

2 bedrooms, 3 beds, 1 bathroom

15–22 Aug

Weekly discount

Free cancellation

5.0 out of 5 average rating, 3 reviews