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Search results; Over 1,000 homes in Chebeague Island

Top guest favourite
Yurt in Chebeague Island
Mongolian Yurt on Chebeague Island
1 bedroom, 1 bed, 0.5 shared bathroom
7–12 Sept
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4.98 out of 5 average rating, 117 reviews
Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 195 reviews
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 house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds, 1 bathroom
26–31 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
2 bedrooms, 3 beds, 1 bathroom
23–30 Aug
4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Harpswell
The Salt Meadow Farm at Harpswell
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Harpswell
Waterfront Cottage On Basin Cove - Amazing Sunsets
3 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
4.98 out of 5 average rating, 236 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
New place to stay
Top guest favourite
Room in Orrs Island
Malaga Island Room
1 double bed, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 133 reviews
Top guest favourite
Guest house in Scarborough
Smith Cottage Higgins Beach
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Oct
4.98 out of 5 average rating, 130 reviews
Guest favourite
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, 6 reviews
Top guest favourite
Cottage in Pownal
Dreamy Post&Beam Hideaway Near Portland & Freeport
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 470 reviews
Top guest favourite
Home in Yarmouth
Peaceful retreat in Yarmouth
2 bedrooms, 2 double beds, 1 bathroom
17–22 Aug
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Home in Scarborough
Higgins Beach *New* Beach Home & Private Offices
3 bedrooms, 4 beds, 1.5 bathrooms
15–20 Dec
5.0 out of 5 average rating, 115 reviews
Top guest favourite
Home in Cape Elizabeth
Pastoral Tranquil Walk to Trails Dining Shopping
3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 36 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
Tiny home in Scarborough
Cozy Tiny Cottage • 9mi Portland • 6mi Beach
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.98 out of 5 average rating, 128 reviews
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 queen beds, 1.5 bathrooms
28 Aug – 2 Sept