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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
30 Aug – 4 Sept
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4.98 out of 5 average rating, 190 reviews
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed, 1 bathroom
10–15 Sept
Top 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, 11 reviews
Guest favourite
Home in Portland
Island Getaway, Short ferry ride to Portland
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Guest house in Scarborough
Smith Cottage Higgins Beach
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 130 reviews
Top guest favourite
Room in Orrs Island
The Reading Room
1 double bed, 1 bathroom
27 Jul – 1 Aug
4.97 out of 5 average rating, 62 reviews
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Scarborough
Higgins Beach studio
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Cottage in Scarborough
2 Bedroom Cottage - Walk to the beach in 2 minutes
2 bedrooms, 3 beds, 1.5 bathrooms
28 Aug – 4 Sept
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Home in Falmouth
The little blue cottage
2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest suite in Falmouth
Pristine Waterfront Studio Apt. Retreat
2 double beds, 1 bathroom
22–27 Aug
4.94 out of 5 average rating, 265 reviews
Top guest favourite
Room in Falmouth
Green Room at Foreside Farmhouse
1 bed, 1.5 bathrooms
26–31 Jul
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Place to stay in Portland
Top of Portland's Munjoy Hill
2 bedrooms, 2 beds, 1 bathroom
16–21 Nov
4.92 out of 5 average rating, 1229 reviews
Top guest favourite
Room in Freeport
Freeport, Maine
1 queen bed, 1 bathroom
17–22 Oct
4.96 out of 5 average rating, 274 reviews
Home in Harpswell
Waterfront Sanctuary
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
New place to stay
Top guest favourite
Room in Orrs Island
Malaga Island Room
1 double bed, 1 bathroom
22–27 Aug
4.92 out of 5 average rating, 130 reviews
Guest favourite
Cottage in Harpswell
Sunset Saltbox on Basin Cove
3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.89 out of 5 average rating, 27 reviews
Top guest favourite
Guest suite in South Portland
Bright Guest Studio Near Lighthouses and Beach
1 bathroom
26–31 Oct
4.99 out of 5 average rating, 321 reviews
Superhost
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews