filters

Search results; Over 1,000 homes in Chebeague Island

Photo 1 of 29
Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
,
4.99 out of 5 average rating, 205 reviews
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 29
Guest favourite
Home in Chebeague Island
Red House
3 bedrooms, 6 beds, 1.5 bathrooms
22–27 Sept
4.92 out of 5 average rating, 24 reviews
Photo 1 of 29
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
Photo 1 of 29
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, 127 reviews
Photo 1 of 29
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
Photo 1 of 29
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
2–9 Oct
Photo 1 of 29
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, 6 reviews
Photo 1 of 29
Superhost
Home in Harpswell
Renovated New Englander home on Orr's Island.
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 5 reviews
Photo 1 of 21
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
Photo 1 of 29
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
Photo 1 of 12
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
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Cabin in Harpswell
Waterledge Cottage - Orrs Island, Maine
4 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 36 reviews
Photo 1 of 29
Superhost
Home in Harpswell
Spacious 5BR Cottage w/Pool, Water & Resort Access
6 bedrooms, 9 beds, 4 bathrooms
22–27 Sept
5.0 out of 5 average rating, 4 reviews
Photo 1 of 18
Guest favourite
Home in Harpswell
Little Harbor Cottage
5 bedrooms, 7 beds, 2.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 13 reviews
Photo 1 of 20
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
22–27 Sept
Photo 1 of 29
Top guest favourite
Home in Harpswell
Peaceful Oceanfront Home W/ Dock & Sunrise Views
5 bedrooms, 7 beds, 4 bathrooms
13–18 Oct
5.0 out of 5 average rating, 7 reviews