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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
6–11 Sept
,
4.91 out of 5 average rating, 46 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
New place to stay
Guest favourite
Cottage in Long Island
A Once in a Lifetime Oceanfront Escape
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
New place to stay
Home in Long Island
Spacious Long Island Retreat
4 bedrooms, 8 beds, 2 bathrooms
9–14 Sept
Guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Cape Elizabeth
Cape Elizabeth Garden Apt+Beach+Close to Portland!
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 308 reviews
Top guest favourite
Home in Portland
Modern Peaks Island Getaway | Ocean Views + Decks
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Room in South Portland
Suite at a convenient location; near Old Port.
1 king bed, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 53 reviews
Top guest favourite
Flat in South Portland
The Nest
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 46 reviews
Superhost
Home in Portland
Gull Cottage: A Classic Peaks Island Charmer
3 bedrooms, 4 beds, 1 bathroom
6–13 Sept
Guest favourite
Flat in South Portland
Peaceful & minutes from Old Port w/private parking
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.91 out of 5 average rating, 85 reviews
Top guest favourite
Flat in Peaks Island
Beach Front, Waterfront, Ferry Beach
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 46 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
Cottage in Portland
Casco-Vista, Island Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Room in Freeport
Limoges - A short walk to shops and has Wifi
1 queen bed, 1.5 bathrooms
9–14 Aug
4.99 out of 5 average rating, 220 reviews
Guest favourite
Home in Biddeford
Luxurious Beachfront New England Home
3 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
4.93 out of 5 average rating, 42 reviews
Top guest favourite
Home in Portland
Ocean view cottage Peaks Island
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Room in Falmouth
Green Room at Foreside Farmhouse
1 bed, 1.5 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 91 reviews