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Search results; Over 1,000 homes in Chebeague Island

Guest favourite
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 bed, 1 private bathroom
20–25 Feb
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5.0 out of 5 average rating, 7 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
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Cottage in Chebeague Island
The Boathouse
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
4.89 out of 5 average rating, 18 reviews
Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 203 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
Top guest favourite
Yurt in Chebeague Island
Mongolian Yurt on Chebeague Island
1 bedroom, 1 bed, WC
13–18 Sept
4.98 out of 5 average rating, 126 reviews
Top guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Harpswell
Spacious 5BR Cottage w/Pool, Water & Resort Access
6 bedrooms, 9 beds, 4 bathrooms
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
20–25 Oct
4.95 out of 5 average rating, 376 reviews
Top guest favourite
Home in Portland
Top Deck - Portland Property with Views!
3 bedrooms, 10 beds, 2.5 bathrooms
25–30 Oct
4.92 out of 5 average rating, 304 reviews
Flat in Brunswick
Hidden Lane 2BR | Charming Apartment Near Bowdoin
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
New place to stay
Superhost
Cottage in Harpswell
A sweet cottage on a pebbly beachfront.
1 bedroom, 1 queen bed, 1 bathroom
30 Apr – 5 May
Guest favourite
Home in Harpswell
The Salt Meadow Farm at Harpswell
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Yarmouth
Luxe 5 Bed/ 3 Bath with Game Room, AC
5 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Flat in Harpswell
Bird Watching Paradise Harpswell
1 bedroom, 2 beds, 1 bathroom
17–22 Sept
4.97 out of 5 average rating, 36 reviews
Home in Harpswell
Stover's Cove Beach Coastal Retreat
6 bedrooms, 8 beds, 3 bathrooms
25–30 Oct
4.69 out of 5 average rating, 51 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Sept
Superhost
Home in Yarmouth
Beautiful home on Broad Cove
4 bedrooms, 4 beds, 3.5 bathrooms
16–21 Sept