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Search results; Over 1,000 homes in Long Island

Superhost
Cottage in Long Island
Grace Cottage
2 bedrooms, 5 beds, 2 private bathrooms
14–19 Sept
,
4.92 out of 5 average rating, 50 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
22–29 Sept
Guest favourite
Cottage in Long Island
Picturesque Maine water view Long Island
4 bedrooms, 5 beds, 1 bathroom
27 Sept – 4 Oct
4.82 out of 5 average rating, 51 reviews
Guest favourite
Cottage in Long Island
A Once in a Lifetime Oceanfront Escape
2 bedrooms, 3 beds, 1 bathroom
16–22 Sept
5.0 out of 5 average rating, 5 reviews
Townhouse in Long Island
Maine Island Escape - close to Portland!
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Yarmouth
Beautiful home on Broad Cove
4 bedrooms, 4 beds, 3.5 bathrooms
17–22 Sept
Top guest favourite
Home in Portland
Cheerful, Sunny, 3 Bedroom Island Home
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 67 reviews
Home in Portland
Island Home, Sleeps 5-8; Close to beach/ferry
6 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Portland
The Island House
3 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
Superhost
Home in Portland
Classic Charm, Ocean View
5 bedrooms, 7 beds, 2 bathrooms
28 Sept – 3 Oct
Cottage in Portland
Dream Maine Cottage on Peaks Island
3 bedrooms, 8 beds, 1.5 bathrooms
21–28 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Portland
Casco-Vista, Island Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 29 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Sept
Home in Peaks Island
Peaks Island, Maine, Northcliffe Cottage
3 bedrooms, 5 beds, 1 bathroom
20–27 Sept
4.83 out of 5 average rating, 18 reviews
Top guest favourite
Cottage in Portland
Captain's Quarters on Peaks Island
1 bedroom, 1 bed, 1 bathroom
1–6 Jan
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Home in Portland
Modern Peaks Island Getaway | Ocean Views + Decks
2 bedrooms, 3 beds, 2 bathrooms
21–26 Nov
5.0 out of 5 average rating, 15 reviews
Guest favourite
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed, 1 bathroom
20–25 Feb
5.0 out of 5 average rating, 7 reviews
Cottage in Portland
Spectacular Direct Oceanfront New Modern Home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.7 out of 5 average rating, 20 reviews
Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 204 reviews