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Search results; Over 1,000 homes in Chebeague Island

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Top guest favourite
Yurt in Chebeague Island
Mongolian Yurt on Chebeague Island
1 bedroom, 1 bed, 0.5 shared bathroom
8–13 Oct
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4.98 out of 5 average rating, 128 reviews
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Guest favourite
Home in Chebeague Island
Timber-Framed Island Home, Sleeps 8
4 bedrooms, 4 beds, 3 bathrooms
13–18 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 206 reviews
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Guest favourite
Cottage in Chebeague Island
The Boathouse
3 bedrooms, 4 beds, 1.5 bathrooms
5–10 Oct
4.89 out of 5 average rating, 18 reviews
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Guest favourite
Home in Chebeague Island
Red House
3 bedrooms, 6 beds, 1.5 bathrooms
1–6 Oct
4.92 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Harpswell
Waterfront Cottage On Basin Cove - Amazing Sunsets
3 bedrooms, 4 beds, 1.5 bathrooms
18–23 Oct
4.98 out of 5 average rating, 244 reviews
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Top guest favourite
Guest house in Scarborough
Smith Cottage Higgins Beach
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 135 reviews
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Top guest favourite
Cottage in Harpswell
Updated Historic Cottage, Private Waterfront, 5BR
5 bedrooms, 7 beds, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 19 reviews
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Superhost
Home in Harpswell
Renovated New Englander home on Orr's Island.
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 5 reviews
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Superhost
Cottage in Harpswell
A charming 2-bedroom cottage with private beach.
2 bedrooms, 3 beds, 1 bathroom
6–11 Oct
4.75 out of 5 average rating, 4 reviews
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Room in Orrs Island
The Reading Room
1 double bed, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 65 reviews
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Guest favourite
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed, 1 bathroom
20–25 Feb
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Harpswell
Brand new year-round oceanfront home with beach.
3 bedrooms, 3 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 114 reviews
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Top guest favourite
Flat in Scarborough
Higgins Beach studio
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Flat in Yarmouth
The Royal Retreat.
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Home in Harpswell
Classic NewEngland Waterfront
5 bedrooms, 9 beds, 3.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Home in Portland
Cheerful, Sunny, 3 Bedroom Island Home
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 67 reviews
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Guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 380 reviews
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Top guest favourite
Cottage in Harpswell
Old fashion neighborhood near the water.
2 bedrooms, 3 beds, 1 bathroom
6–11 Oct
4.96 out of 5 average rating, 69 reviews