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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, 4 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
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
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
Flat in Portland
Back Cove Retreat | Walk, Relax, Explore
2 bedrooms, 2 beds, 1 bathroom
5–10 Oct
New place to stay
Superhost
Cabin in Oxford
Glamping Cabin with Hot Tub and Onsite Sauna
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.96 out of 5 average rating, 365 reviews
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
Home in Yarmouth
Coastal Escape on Cousins Island in Yarmouth
3 bedrooms, 5 beds, 2.5 bathrooms
5–12 Sept
Home in Westbrook
Cozy Cape in the Brook
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest house in West Bath
Spruce Ledge Boathouse
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 57 reviews
Home in Portland
Historic Island Retreat
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
Top guest favourite
Home in Yarmouth
Peaceful retreat in Yarmouth
2 bedrooms, 2 double beds, 1 bathroom
17–22 Aug
4.92 out of 5 average rating, 37 reviews
Top guest favourite
Cottage in Pownal
Dreamy Post&Beam Hideaway Near Portland & Freeport
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 471 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, 64 reviews
Top guest favourite
Flat in Brunswick
Cozy Post & Beam Farmhouse
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews