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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, 191 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
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds, 1 bathroom
1–6 Aug
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 queen beds, 1.5 bathrooms
15–20 Aug
New place to stay
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
New place to stay
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Harpswell
Sunset Stunner w/summer dock
2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Cottage in Phippsburg
#68 Classic Harbor Cottage (aka “Diversion”)
3 bedrooms, 5 beds, 1 bathroom
15–22 Aug
5.0 out of 5 average rating, 12 reviews
Superhost
Cottage in Harpswell
A charming 2-bedroom cottage with private beach.
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.67 out of 5 average rating, 3 reviews
Guest suite in Yarmouth
Ash + Timber | Forest Sauna Suite Near Portland
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Harpswell
Old fashion neighborhood near the water.
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.95 out of 5 average rating, 62 reviews
Top guest favourite
Home in Cape Elizabeth
"Periwinkle" ~ a Charming Oceanfront Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
1–7 Nov
5.0 out of 5 average rating, 35 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, 7 reviews
Home in Yarmouth
Oceanfront Cottage
2 bedrooms, 6 beds, 2 bathrooms
2–9 Jan
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
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
4.99 out of 5 average rating, 78 reviews
Guest favourite
Home in Biddeford
Luxurious Beachfront New England Home
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
4.93 out of 5 average rating, 40 reviews
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.96 out of 5 average rating, 357 reviews