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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, 206 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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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
Yurt in Chebeague Island
Mongolian Yurt on Chebeague Island
1 bedroom, 1 bed, WC
8–13 Oct
4.98 out of 5 average rating, 128 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
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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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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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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Home in Harpswell
Stover's Cove Beach Coastal Retreat
6 bedrooms, 8 beds, 3 bathrooms
2–7 Nov
4.69 out of 5 average rating, 51 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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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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Guest favourite
Home in Harpswell
Little Harbor Cottage
5 bedrooms, 7 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Long Island
Ocean Side Cottage, Steps from the Beach
3 bedrooms, 5 beds, 1 bathroom
1–6 May
5.0 out of 5 average rating, 15 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
With home theater, pool table and ocean views!
4 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.88 out of 5 average rating, 16 reviews
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Guest favourite
Holiday home in Portland
Heron's Perch on Peaks' Island
4 bedrooms, 8 beds, 2 bathrooms
11–16 Oct
4.95 out of 5 average rating, 43 reviews
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Guest favourite
Home in Freeport
Spacious Freeport 5 BR Home | Near LLBean & Coast
5 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
4.94 out of 5 average rating, 139 reviews
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Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
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Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
2–9 Oct