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Search results; Over 1,000 homes in Chebeague Island

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Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
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4.99 out of 5 average rating, 204 reviews
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Guest favourite
Home in Chebeague Island
Timber-Framed Island Home, Sleeps 8
4 bedrooms, 4 beds
13–18 Oct
5.0 out of 5 average rating, 12 reviews
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Cottage in Chebeague Island
The Boathouse
3 bedrooms, 4 beds
17–22 Sept
4.89 out of 5 average rating, 18 reviews
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Top guest favourite
Yurt in Chebeague Island
Mongolian Yurt on Chebeague Island
1 bedroom, 1 bed
11–16 Oct
4.98 out of 5 average rating, 126 reviews
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Top guest favourite
Home in Harpswell
Waterfront Cottage On Basin Cove - Amazing Sunsets
3 bedrooms, 4 beds
18–23 Oct
4.98 out of 5 average rating, 243 reviews
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Guest favourite
Home in Harpswell
Little Harbor Cottage
5 bedrooms, 7 beds
18–23 Sept
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed
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
19–24 Sept
5.0 out of 5 average rating, 114 reviews
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Top guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds
16–21 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Guest house in Scarborough
Smith Cottage Higgins Beach
2 bedrooms, 2 queen beds
25–30 Oct
4.99 out of 5 average rating, 134 reviews
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Top guest favourite
Flat in Scarborough
Higgins Beach studio
1 bedroom, 1 bed
1–6 Oct
5.0 out of 5 average rating, 21 reviews
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Home in Long Island
500Island
4 bedrooms, 5 beds
22–29 Sept
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Top guest favourite
Guest house in Harpswell
The Bird House
2 bedrooms, 2 beds
12–17 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Cabin in Harpswell
Waterledge Cottage - Orrs Island, Maine
4 bedrooms, 4 beds
17–22 Sept
4.97 out of 5 average rating, 36 reviews
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Top guest favourite
Room in Orrs Island
The Reading Room
1 double bed
27 Sept – 2 Oct
4.97 out of 5 average rating, 65 reviews
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Top guest favourite
Cottage in Harpswell
Old fashion neighborhood near the water.
2 bedrooms, 3 beds
23–28 Sept
4.96 out of 5 average rating, 68 reviews
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Flat in Brunswick
Hidden Lane 2BR | Charming Apartment Near Bowdoin
2 bedrooms, 2 beds
27 Sept – 2 Oct
New place to stay
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Superhost
Cabin in Harpswell
Beautiful log home on ocean with large deck & yard
3 bedrooms, 5 beds
18–23 Oct
4.93 out of 5 average rating, 14 reviews