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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, 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
10–15 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
1–6 Aug
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, 235 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
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
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
New place to stay
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, 5 reviews
Top guest favourite
Tiny home in Freeport
The Craic House Maine #mainethewaylifeshouldbe
1 bedroom, 1 king bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cabin in Freeport
Nature view cabin in the pines w/ full bath - 05
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Cabin in Yarmouth
Woodland Cottage
1 queen bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 8 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
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 queen beds, 1.5 bathrooms
28 Aug – 2 Sept
Top guest favourite
Home in Harpswell
Oceanfront Cottage w/ Wharf & Kayaks – Harpswell
2 bedrooms, 2 beds, 1 bathroom
26 Sept – 3 Oct
5.0 out of 5 average rating, 22 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, 8 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
Superhost
Home in Harpswell
The Beach Pea - Waterfront cottage, Pet Friendly!
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 3 reviews