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Search results; Over 1,000 homes in Long Island

Guest favourite
Cottage in Long Island
Picturesque Maine water view Long Island
4 bedrooms, 5 beds, 1 private bathroom
27 Sept – 4 Oct
,
4.82 out of 5 average rating, 50 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 Long Island
Spacious Long Island Retreat
4 bedrooms, 8 beds, 2 bathrooms
9–14 Sept
Superhost
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
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
New place to stay
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, 27 reviews
Superhost
Home in Portland
Gull Cottage: A Classic Peaks Island Charmer
3 bedrooms, 4 beds, 1 bathroom
6–13 Sept
Superhost
Home in Harpswell
The Beach Pea - Waterfront cottage, Pet Friendly!
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 3 reviews
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 3 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
Cottage in Portland
Spectacular Direct Oceanfront New Modern Home
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.7 out of 5 average rating, 20 reviews
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
4.98 out of 5 average rating, 80 reviews
Superhost
Home in Freeport
Casco Bay Beachfront Retreat
3 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
New place to stay
Top guest favourite
Flat in South Portland
Forest City Oasis and Spa/Beaches/Portland/Pets!
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cabin in Gray
Chickadee Cottage
2 bedrooms, 4 beds, 1 bathroom
12–17 Jun
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Harpswell
The Salt Meadow Farm at Harpswell
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Tiny home in Portland
The Garden Cabin Tiny Home
1 bedroom, 1 double bed, 1.5 bathrooms
1–6 Dec
4.95 out of 5 average rating, 548 reviews
Top guest favourite
Home in Cape Elizabeth
Pastoral Tranquil Walk to Trails Dining Shopping
3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 34 reviews