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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
Cottage in Chebeague Island
The Boathouse
3 bedrooms, 4 beds, 1.5 bathrooms
15–20 Sept
4.89 out of 5 average rating, 18 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
Top guest favourite
Cabin in Harpswell
Waterledge Cottage - Orrs Island, Maine
4 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.97 out of 5 average rating, 36 reviews
Guest favourite
Cottage in Scarborough
2 Bedroom Cottage - Walk to the beach in 2 minutes
2 bedrooms, 3 beds, 1.5 bathrooms
9–16 Oct
4.94 out of 5 average rating, 36 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
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
Home in Harpswell
Lovely Coastal Cottage on Quiet Cove
2 bedrooms, 3 beds, 2 bathrooms
9–14 Nov
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Cottage in Harpswell
"Footnote" A unique quintessential Maine cottage.
2 bedrooms, 3 beds, 1 bathroom
29 Sept – 4 Oct
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Cottage in Harpswell
Seaside-The way life should be!
2 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 26 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 Harpswell
Slack Tide
1 bedroom, 1 king bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Guest suite in Phippsburg
Apartment w/kitchen on the Ocean!
1 bedroom, 1 queen bed, 1 bathroom
22–27 Sept
4.95 out of 5 average rating, 260 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
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, 14 reviews
Top guest favourite
Guest house in West Bath
Spruce Ledge Boathouse
1 bedroom, 3 beds, 1 bathroom
15–20 May
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Home in Scarborough
Lobster Boats & Harbor View Pine Point Home
3 bedrooms, 5 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 38 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
Flat in Cape Elizabeth
Cape Elizabeth Garden Apt+Beach+Close to Portland!
1 bedroom, 3 beds, 1 bathroom
27 Oct – 1 Nov
4.99 out of 5 average rating, 311 reviews