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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
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Harpswell
The Beach Pea - Waterfront cottage, Pet Friendly!
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Cottage in Long Island
Long Island Cottage: The Lobster Trap
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 79 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
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
New place to stay
Guest favourite
Home in Harpswell
The Salt Meadow Farm at Harpswell
4 bedrooms, 5 beds, 2.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Freeport
Casco Bay Beachfront Retreat
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Georgetown
Cottage on Todd Bay
3 bedrooms, 4 beds, 1.5 bathrooms
5–10 Oct
4.98 out of 5 average rating, 151 reviews
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
4.96 out of 5 average rating, 365 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, 37 reviews
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 queen beds, 1.5 bathrooms
22–27 Sept
Top guest favourite
Flat in Harpswell
Bird Watching Paradise Harpswell
1 bedroom, 2 beds, 1 bathroom
17–22 Sept
4.97 out of 5 average rating, 33 reviews
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
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
Top guest favourite
Home in Harpswell
Oceanfront Cottage w/ Wharf & Kayaks – Harpswell
2 bedrooms, 2 beds, 1 bathroom
3–10 Oct
5.0 out of 5 average rating, 23 reviews
Home in Portland
Charming house near downtown and comfortable.
3 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 5 reviews