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Search results; Over 1,000 homes in Long Island

Superhost
Cottage in Long Island
Maine island vacation cottage
3 bedrooms, 4 beds, 1.5 private bathrooms
31 Aug – 7 Sept
,
4.62 out of 5 average rating, 60 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
Cottage in Long Island
Long Island Cottage: The Lobster Trap
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 79 reviews
Townhouse in Long Island
Maine Island Escape - close to Portland!
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
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
Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 198 reviews
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, 11 reviews
Townhouse in Portland
Coastal Island Retreat in Diamond Cove, Casco Bay
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.98 out of 5 average rating, 84 reviews
Top guest favourite
Home in Cape Elizabeth
Pastoral Tranquil Walk to Trails Dining Shopping
3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 37 reviews
Superhost
Home in Portland
Unbeatable view! Peaceful spot.
4 bedrooms, 2 double beds, 2 bathrooms
7–12 Oct
5.0 out of 5 average rating, 4 reviews
Top 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, 9 reviews
Top guest favourite
Cabin in Oxford
Glamping Cabin with Hot Tub and Onsite Sauna
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Scarborough
Higgins Beach *New* Beach Home & Private Offices
3 bedrooms, 4 beds, 1.5 bathrooms
15–20 Dec
5.0 out of 5 average rating, 115 reviews
Flat in Yarmouth
The Royal Retreat.
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Chebeague Island
The Boathouse
3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Aug
4.89 out of 5 average rating, 18 reviews
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds, 1 bathroom
7–12 Nov
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Portland
Ocean Paradise Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds, 1.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 84 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