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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
10–15 Aug
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4.98 out of 5 average rating, 190 reviews
Top guest favourite
Home in Chebeague Island
Timber-Framed Island Home, Sleeps 8
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 4 beds, 3 bathrooms
5–10 Oct
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 bed, 1 bathroom
10–15 Sept
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds, 1 bathroom
17–22 Jul
Top guest favourite
Home in Harpswell
Waterfront Cottage On Basin Cove - Amazing Sunsets
4.98 out of 5 average rating, 233 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
Top guest favourite
Guest house in Scarborough
Smith Cottage Higgins Beach
4.98 out of 5 average rating, 130 reviews, 2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
4.97 out of 5 average rating, 39 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
Home in Falmouth
The little blue cottage
5.0 out of 5 average rating, 4 reviews, 2 beds, 1 bathroom
26–31 Aug
Top guest favourite
Home in Harpswell
Sunset Stunner w/summer dock
4.97 out of 5 average rating, 31 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Aug
Guest favourite
Flat in Harpswell
Bird Watching Paradise Harpswell
5.0 out of 5 average rating, 28 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Jul – 2 Aug
Superhost
Bed and breakfast in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Cabin in Yarmouth
Woodland Cottage
5.0 out of 5 average rating, 5 reviews, 1 bed, 1 bathroom
13–18 Sept
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
4.99 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
Home in Phippsburg
Lovely 3-bedrom cottage with deep water dock.
3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Guest favourite
Home in Portland
Island Getaway, Short ferry ride to Portland
5.0 out of 5 average rating, 22 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Sept
Guest favourite
Loft in Harpswell
Oceanfront Studio w/ Private Dock in Harpswell!
5.0 out of 5 average rating, 7 reviews, 1 bed, 1 bathroom
21–26 Aug
Top guest favourite
Home in Georgetown
Cottage on Todd Bay
4.98 out of 5 average rating, 149 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
22–27 Sept
Top guest favourite
Treehouse in Pownal
The Copper Fox Treehouse
4.99 out of 5 average rating, 178 reviews, 1 bedroom, 3 beds, 1 bathroom
26–31 Aug