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Search results; Over 1,000 homes in Chebeague Island

Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 bed, 1 private bathroom
30 Aug – 4 Sept
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4.98 out of 5 average rating, 192 reviews
Top guest favourite
Home in Chebeague Island
Timber-Framed Island Home, Sleeps 8
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 4 beds, 3 bathrooms
13–18 Oct
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 bed, 1 bathroom
10–15 Sept
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
4.97 out of 5 average rating, 39 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds, 1 bathroom
1–6 Aug
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 beds, 1.5 bathrooms
28 Aug – 4 Sept
Home in Long Island
500Island
New place to stay, 4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
Top guest favourite
Home in Harpswell
Sunset Stunner w/summer dock
4.97 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
Guest favourite
Cottage in Harpswell
Sunset Saltbox on Basin Cove
4.89 out of 5 average rating, 27 reviews, 3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
Top guest favourite
Guest house in Scarborough
Smith Cottage Higgins Beach
4.98 out of 5 average rating, 130 reviews, 2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
Top guest favourite
Cottage in Harpswell
Old fashion neighborhood near the water.
4.95 out of 5 average rating, 62 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
Home in Yarmouth
Oceanfront Cottage
2 bedrooms, 6 beds, 2 bathrooms
2–9 Jan
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
12–17 Aug
Top guest favourite
Cabin in Gray
Chickadee Cottage
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Jun
Guest favourite
Home in Portland
Island Getaway, Short ferry ride to Portland
5.0 out of 5 average rating, 23 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Sept
Top guest favourite
Room in Orrs Island
Malaga Island Room
4.92 out of 5 average rating, 130 reviews, 1 double bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Tiny home in Freeport
Cozy Rock Cabin #thewaylifeshouldbe
4.99 out of 5 average rating, 382 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
4.96 out of 5 average rating, 357 reviews, 3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Cottage in Portland
Spectacular Direct Oceanfront New Modern Home
4.7 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 1 bathroom
7–12 Sept