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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
4 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 11 reviews
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed
10–15 Sept
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds
17–22 Jul
Top guest favourite
Home in Harpswell
Waterfront Cottage On Basin Cove - Amazing Sunsets
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 233 reviews
Top guest favourite
Guest house in Scarborough
Smith Cottage Higgins Beach
2 bedrooms, 2 queen beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 130 reviews
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 queen beds
15–20 Aug
New place to stay
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
2 bedrooms, 3 beds
22–27 Aug
4.97 out of 5 average rating, 39 reviews
Guest favourite
Flat in Harpswell
Bird Watching Paradise Harpswell
1 bedroom, 2 beds
28 Jul – 2 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Treehouse in Pownal
The Copper Fox Treehouse
1 bedroom, 3 beds
26–31 Aug
4.99 out of 5 average rating, 178 reviews
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds
18–23 Oct
4.99 out of 5 average rating, 76 reviews
Superhost
Bed and breakfast in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bedroom, 1 bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
2 bedrooms, 6 beds
8–13 Aug
Top guest favourite
Cabin in Yarmouth
Woodland Cottage
1 queen bed
28 Sept – 3 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Georgetown
Cottage on Todd Bay
3 bedrooms, 4 beds
22–27 Sept
4.98 out of 5 average rating, 149 reviews
Top guest favourite
Cottage in Harpswell
Old fashion neighborhood near the water.
2 bedrooms, 3 beds
25–30 Aug
4.95 out of 5 average rating, 62 reviews
Guest favourite
Loft in Harpswell
Oceanfront Studio w/ Private Dock in Harpswell!
1 queen bed
21–26 Aug
5.0 out of 5 average rating, 7 reviews
Home in Yarmouth
Oceanfront Cottage
2 bedrooms, 6 beds
2–9 Jan
Top guest favourite
Home in Freeport
Waterfront Coastal Retreat | 8 Acres | Near LLBean
4 bedrooms, 6 beds
10–15 Aug
4.9 out of 5 average rating, 73 reviews