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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
4–9 Oct
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4.99 out of 5 average rating, 204 reviews
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
Guest favourite
Cottage in Chebeague Island
The Boathouse
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Sept
4.89 out of 5 average rating, 18 reviews
Top guest favourite
Yurt in Chebeague Island
Mongolian Yurt on Chebeague Island
1 bedroom, 1 bed, WC
11–16 Oct
4.98 out of 5 average rating, 126 reviews
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, 243 reviews
Guest favourite
Home in Harpswell
Little Harbor Cottage
5 bedrooms, 7 beds, 2.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 12 reviews
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
Top guest favourite
Home in Harpswell
Brand new year-round oceanfront home with beach.
3 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 114 reviews
Top guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 18 reviews
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
Top guest favourite
Cabin in Harpswell
Waterledge Cottage - Orrs Island, Maine
4 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.97 out of 5 average rating, 36 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Sept
Superhost
Home in Harpswell
Spacious 5BR Cottage w/Pool, Water & Resort Access
6 bedrooms, 9 beds, 4 bathrooms
17–22 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Harpswell
With home theater, pool table and ocean views!
4 bedrooms, 5 beds, 3 bathrooms
26 Sept – 1 Oct
4.88 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Harpswell
Old fashion neighborhood near the water.
2 bedrooms, 3 beds, 1 bathroom
23–28 Sept
4.96 out of 5 average rating, 67 reviews
Top guest favourite
Guest house in Scarborough
Smith Cottage Higgins Beach
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 133 reviews
Guest favourite
Cottage in Harpswell
Sunset Saltbox on Basin Cove
3 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
4.9 out of 5 average rating, 30 reviews
Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 75 reviews
Flat in Brunswick
Hidden Lane 2BR | Charming Apartment Near Bowdoin
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
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