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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
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, 4 reviews
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed, 1 bathroom
10–15 Sept
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
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, 190 reviews
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 queen beds, 1.5 bathrooms
15–20 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, 25 reviews
Superhost
Home in Raymond
Renovated New Waterfront Cottage on Crescent Lake!
2 bedrooms, 3 beds, 1 bathroom
27 Aug – 1 Sept
New place to stay
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 7 reviews
Home in Raymond
Cozy Maine Camp on Private Peninsula
3 bedrooms, 4 beds, 1 bathroom
1–6 Aug
New place to stay
Guest favourite
Cottage in Portland
Peaks Island Waterfront
1 bedroom, 1 double bed, 1 bathroom
30 Aug – 4 Sept
4.93 out of 5 average rating, 118 reviews
Guest favourite
Flat in Brunswick
Cozy Post & Beam Farmhouse
2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 9 reviews
Guest suite in Yarmouth
Ash + Timber | Forest Sauna Suite Near Portland
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 4 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, 34 reviews
Top guest favourite
Home in Portland
Wall St. Retreat: Family-Ready Portland Home
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 19 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
29 Jul – 3 Aug
New place to stay