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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
Home in Long Island
500Island
4 bedrooms, 5 beds
23–30 Aug
New place to stay
Guest favourite
Cottage in Long Island
A Once in a Lifetime Oceanfront Escape
2 bedrooms, 3 beds
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Home in Long Island
Spacious Long Island Retreat
4 bedrooms, 8 beds
9–14 Sept
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed
27 Aug – 1 Sept
5.0 out of 5 average rating, 3 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds
23–28 Aug
New place to stay
Guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cottage in Portland
Casco-Vista, Island Cottage
3 bedrooms, 3 beds
6–11 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Tiny home in Freeport
Cozy Rock Cabin #thewaylifeshouldbe
2 bedrooms, 2 beds
28 Aug – 2 Sept
4.99 out of 5 average rating, 386 reviews
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds
18–23 Oct
4.98 out of 5 average rating, 81 reviews
Superhost
Cabin in Oxford
Glamping Cabin with Hot Tub and Onsite Sauna
1 bedroom, 1 king bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Flat in South Portland
Willard Beach 2-BR Coastal Apt w/ Full Kitchen
2 bedrooms, 3 beds
31 Aug – 5 Sept
New place to stay
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds
28 Aug – 2 Sept
4.96 out of 5 average rating, 365 reviews
Superhost
Home in Portland
Gull Cottage: A Classic Peaks Island Charmer
3 bedrooms, 4 beds
27 Sept – 2 Oct
Top guest favourite
Home in Falmouth
The little blue cottage
2 beds
8–13 Sept
5.0 out of 5 average rating, 9 reviews
Home in Westbrook
Cozy Cape in the Brook
2 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Portland
The Yankee Dugout
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 196 reviews
Top guest favourite
Home in Harpswell
Sunset Stunner w/summer dock
2 bedrooms, 2 beds
25–30 Oct
4.97 out of 5 average rating, 35 reviews
Home in Kennebunk
Private, family friendly getaway.
3 bedrooms, 8 beds
19–24 Oct
5.0 out of 5 average rating, 4 reviews