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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 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
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Portland
Gull Cottage: A Classic Peaks Island Charmer
3 bedrooms, 4 beds, 1 bathroom
6–13 Sept
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
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, 35 reviews
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
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
4.96 out of 5 average rating, 360 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
Top guest favourite
Home in Falmouth
The little blue cottage
2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Portland
Island Getaway, Short ferry ride to Portland
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 23 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
Flat in Portland
The Yankee Dugout
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 194 reviews
Top guest favourite
Home in Yarmouth
Luxe 5 Bed/ 3 Bath with Game Room, AC
5 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 11 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
Home in Harpswell
Sunset Stunner w/summer dock
2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 33 reviews