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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
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, 3 reviews
Top guest favourite
Guest house in Scarborough
Smith Cottage Higgins Beach
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Oct
4.98 out of 5 average rating, 130 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 favourite
Cottage in Scarborough
2 Bedroom Cottage - Walk to the beach in 2 minutes
2 bedrooms, 3 beds, 1.5 bathrooms
28 Aug – 4 Sept
4.94 out of 5 average rating, 35 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
New place to stay
Top guest favourite
Home in Cape Elizabeth
"Periwinkle" ~ a Charming Oceanfront Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
19–25 Sept
5.0 out of 5 average rating, 35 reviews
Guest favourite
Home in Harpswell
The Salt Meadow Farm at Harpswell
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Scarborough
Higgins Beach studio
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed, 1 bathroom
30 Aug – 4 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, 1 bathroom
1–6 Aug
Guest favourite
Cabin in Yarmouth
Woodland Cottage
1 queen bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in South Portland
Bright Guest Studio Near Lighthouses and Beach
1 bathroom
6–11 Nov
4.99 out of 5 average rating, 323 reviews
Top guest favourite
Guest suite in South Portland
Oceanfront with amazing views and private entrance
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.99 out of 5 average rating, 898 reviews
Top guest favourite
Room in Freeport
Limoges - A short walk to shops and has Wifi
1 queen bed, 1.5 bathrooms
9–14 Aug
4.99 out of 5 average rating, 219 reviews
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Harpswell
Treehouse Farm Stay on the Maine Coast
1 bedroom, 1 king bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in South Portland
Peaceful & minutes from Old Port w/private parking
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.91 out of 5 average rating, 85 reviews
Top guest favourite
Flat in Cape Elizabeth
Cape Elizabeth Garden Apt+Beach+Close to Portland!
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 308 reviews