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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
21–26 Aug
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4.98 out of 5 average rating, 198 reviews
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
Top guest favourite
Yurt in Chebeague Island
Mongolian Yurt on Chebeague Island
1 bedroom, 1 bed
7–12 Sept
4.98 out of 5 average rating, 122 reviews
Guest favourite
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed
10–15 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
2 bedrooms, 3 beds
23–30 Aug
4.98 out of 5 average rating, 40 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds
23–30 Aug
Home in Yarmouth
Coastal Escape on Cousins Island in Yarmouth
3 bedrooms, 5 beds
5–12 Sept
Top guest favourite
Home in Harpswell
Waterfront Cottage On Basin Cove - Amazing Sunsets
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 236 reviews
Top guest favourite
Cabin in Yarmouth
Woodland Cottage
1 queen bed
1–6 Nov
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Harpswell
Sunset Stunner w/summer dock
2 bedrooms, 2 beds
25–30 Oct
4.97 out of 5 average rating, 35 reviews
Guest favourite
Home in Harpswell
The Salt Meadow Farm at Harpswell
4 bedrooms, 5 beds
24–29 Oct
5.0 out of 5 average rating, 14 reviews
Flat in Portland
Back Cove Retreat | Walk, Relax, Explore
2 bedrooms, 2 beds
17–22 Oct
New place to stay
Top guest favourite
Home in Raymond
Lake front home on Little Sebago
4 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Harpswell
Oceanfront Cottage w/ Wharf & Kayaks – Harpswell
2 bedrooms, 2 beds
3–10 Oct
5.0 out of 5 average rating, 23 reviews
Home in Yarmouth
Oceanfront Cottage
2 bedrooms, 6 beds
2–9 Jan
5.0 out of 5 average rating, 3 reviews
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 queen beds
22–27 Sept
Superhost
Home in Raymond
Cozy Modern Lakefront — Foliage, Skiing, Skating
2 bedrooms, 2 beds
21–28 Jun
New place to stay
Top guest favourite
Tiny home in Freeport
Cozy Rock Cabin #thewaylifeshouldbe
2 bedrooms, 2 beds
28 Aug – 2 Sept
4.99 out of 5 average rating, 387 reviews