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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 double bed
10–15 Sept
Top guest favourite
Home in Chebeague Island
Timber-Framed Island Home, Sleeps 8
4 bedrooms, 4 beds
13–18 Oct
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds
1–6 Aug
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
2 bedrooms, 3 beds
22–27 Aug
4.97 out of 5 average rating, 39 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds
23–30 Aug
New place to stay
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds
18–23 Oct
4.99 out of 5 average rating, 78 reviews
Guest favourite
Home in Georgetown
Serene Coveside Cottage
2 bedrooms, 3 beds
2–7 Nov
4.94 out of 5 average rating, 90 reviews
Guest favourite
Cottage in Long Island
Picturesque Maine water view Long Island
4 bedrooms, 5 beds
27 Sept – 4 Oct
4.82 out of 5 average rating, 50 reviews
Guest favourite
Cottage in Harpswell
Sunset Saltbox on Basin Cove
3 bedrooms, 3 beds
6–11 Sept
4.89 out of 5 average rating, 27 reviews
Top guest favourite
Cottage in Harpswell
Old fashion neighborhood near the water.
2 bedrooms, 3 beds
25–30 Aug
4.95 out of 5 average rating, 62 reviews
Top guest favourite
Cottage in Yarmouth
Buoys on Bates | Couples' Cottage near Portland
1 bedroom, 1 queen bed
2–7 Aug
4.96 out of 5 average rating, 175 reviews
Top guest favourite
Flat in Yarmouth
Sweet 1-Bedroom Apartment in Vintage Village Cape
1 bedroom, 1 queen bed
21–26 Sept
4.97 out of 5 average rating, 185 reviews
Top guest favourite
Cabin in Gray
Chickadee Cottage
2 bedrooms, 4 beds
2–7 Jun
5.0 out of 5 average rating, 12 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds
12–17 Aug
New place to stay
Superhost
Home in Raymond
Renovated New Waterfront Cottage on Crescent Lake!
2 bedrooms, 3 beds
27 Aug – 1 Sept
New place to stay
Top guest favourite
Home in Freeport
Waterfront Coastal Retreat | 8 Acres | Near LLBean
4 bedrooms, 6 beds
23–28 Aug
4.91 out of 5 average rating, 74 reviews
Home in Brunswick
The Fuller House
3 bedrooms, 3 queen beds
8–13 Sept
New place to stay
Top guest favourite
Cabin in Boothbay Harbor
Lakeside 3 BR Cabin in Boothbay Harbor
3 bedrooms, 4 beds
13–18 Sept
4.97 out of 5 average rating, 279 reviews