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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, 127 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, 12 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, 205 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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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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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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Guest favourite
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 5 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, 134 reviews
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Guest favourite
Cottage in Long Island
Picturesque Maine water view Long Island
4 bedrooms, 5 beds, 1 bathroom
27 Sept – 2 Oct
4.82 out of 5 average rating, 51 reviews
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Home in Harpswell
Live Well Farm
5 bedrooms, 8 beds, 2.5 bathrooms
7–14 Nov
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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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Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
22–29 Sept
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Superhost
Home in Yarmouth
Beautiful home on Broad Cove
4 bedrooms, 4 beds, 3.5 bathrooms
22–27 Sept
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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, 18 reviews
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Superhost
Cottage in Harpswell
A sweet cottage on a pebbly beachfront.
1 bedroom, 1 queen bed, 1 bathroom
30 Apr – 5 May
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Cottage in Harpswell
Bober Cottage - Quaint cottage intimately set on t
2 bedrooms, 2 beds, 1 bathroom
15–20 Oct
4.83 out of 5 average rating, 12 reviews
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Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
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Top guest favourite
Cabin in Freeport
The Maine Frame | Modern A-Frame Cabin in Freeport
2 bedrooms, 2 beds, 1 bathroom
28 Nov – 3 Dec
5.0 out of 5 average rating, 155 reviews
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Guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 15 reviews