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Search results; Over 1,000 homes in Long Island

Guest favourite
Home in Long Island
Whole house on a great island in Casco Bay!
3 bedrooms, 4 beds, 2 private bathrooms
7–12 Sept
,
4.99 out of 5 average rating, 76 reviews
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
Townhouse in Long Island
Maine Island Escape - close to Portland!
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
New place to stay
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, 8 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
27 Aug – 1 Sept
New place to stay
Flat in Yarmouth
The Royal Retreat.
2 bedrooms, 2 queen beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Wiscasset
Cozy Midcoast Island Cottage
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
Home in Portland
Charming house near downtown and comfortable.
3 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 5 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, 36 reviews
Top guest favourite
Home in Georgetown
Cottage on Todd Bay
3 bedrooms, 4 beds, 1.5 bathrooms
5–10 Oct
4.98 out of 5 average rating, 151 reviews
Top guest favourite
Guest suite in Yarmouth
Ash + Timber | Forest Sauna Suite Near Portland
1 bedroom, 2 beds, 1 bathroom
20–25 Oct
5.0 out of 5 average rating, 7 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, 195 reviews
Superhost
Home in Harpswell
The Beach Pea - Waterfront cottage, Pet Friendly!
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Biddeford
King Bedroom at Thistle Pond. Close to UNE & Beach
1 king bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 71 reviews
Top guest favourite
Tiny home in Durham
Crow’s Nest Tiny House at Old Crow Ranch
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 392 reviews
Top guest favourite
Tiny home in Scarborough
Cozy Tiny Cottage • 9mi Portland • 6mi Beach
1 bedroom, 2 beds, 1 bathroom
3–8 Nov
4.98 out of 5 average rating, 129 reviews
Home in Phippsburg
The Little House in Phippsburg
2 bedrooms, 3 beds, 1 bathroom
3–8 Sept
New place to stay
Top guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 14 reviews