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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, 193 reviews
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 bed, 1 bathroom
10–15 Sept
Top guest favourite
Home in Chebeague Island
Timber-Framed Island Home, Sleeps 8
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 4 beds, 3 bathrooms
13–18 Oct
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds, 1 bathroom
1–6 Aug
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
4.97 out of 5 average rating, 39 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
Home in Long Island
500Island
New place to stay, 4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
4.97 out of 5 average rating, 79 reviews, 3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
Guest favourite
Home in Georgetown
Serene Coveside Cottage
4.94 out of 5 average rating, 90 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Nov
Top guest favourite
Home in Yarmouth
Peaceful retreat in Yarmouth
4.92 out of 5 average rating, 36 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Guest favourite
Home in Harpswell
The Salt Meadow Farm at Harpswell
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Oct
Top guest favourite
Cabin in Boothbay Harbor
Lakeside 3 BR Cabin in Boothbay Harbor
4.97 out of 5 average rating, 279 reviews, 3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
Guest favourite
Guest suite in Yarmouth
Ash + Timber | Forest Sauna Suite Near Portland
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Oct
Top guest favourite
Cabin in Gray
Chickadee Cottage
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Jun
Top guest favourite
Flat in Yarmouth
Sweet 1-Bedroom Apartment in Vintage Village Cape
4.97 out of 5 average rating, 185 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Sept
Superhost
Cottage in Harpswell
A charming 2-bedroom cottage with private beach.
4.67 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
Home in Brunswick
Oceanfront Cottage on Mere Point, Maine
3 bedrooms, 4 beds, 2 bathrooms
15–21 Aug
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 beds, 1.5 bathrooms
28 Aug – 4 Sept
Superhost
Home in Raymond
Renovated New Waterfront Cottage on Crescent Lake!
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
27 Aug – 1 Sept
Superhost
Home in Harpswell
Panoramic ocean views from sunrise to sunset!
New place to stay, 2 bedrooms, 4 beds, 2 bathrooms
22–27 Aug