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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
27 Aug – 1 Sept
5.0 out of 5 average rating, 3 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
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
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
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
Superhost
Home in Harpswell
The Beach Pea - Waterfront cottage, Pet Friendly!
2 bedrooms, 3 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds, 1 bathroom
17–22 Aug
Top guest favourite
Home in Harpswell
Oceanfront Cottage w/ Wharf & Kayaks – Harpswell
2 bedrooms, 2 beds, 1 bathroom
26 Sept – 3 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Room in Freeport
Limoges - A short walk to shops and has Wifi
1 queen bed, 1.5 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 221 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, 324 reviews
Top guest favourite
Room in Falmouth
Swedish Room in Foreside Farmhouse
1 queen bed, 1 bathroom
14–19 Sept
4.93 out of 5 average rating, 113 reviews
Superhost
Cottage in Harpswell
A sweet cottage on a pebbly beachfront.
1 bedroom, 1 queen bed, 1 bathroom
30 Apr – 5 May
Guest favourite
Cottage in Harpswell
Dockside Cottage at Lookout Point
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Place to stay in Portland
Top of Portland's Munjoy Hill
2 bedrooms, 2 beds, 1 bathroom
16–21 Nov
4.92 out of 5 average rating, 1232 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
New place to stay
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, 6 reviews
Top guest favourite
Guest suite in Falmouth
Pristine Waterfront Studio Apt. Retreat
2 double beds, 1 bathroom
29 Aug – 3 Sept
4.94 out of 5 average rating, 269 reviews
Top guest favourite
Flat in Portland
Old Port / Parking / Patio
1 bedroom, 1 queen bed, 1 bathroom
22–27 Nov
4.99 out of 5 average rating, 850 reviews