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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, 194 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
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 queen beds, 1.5 bathrooms
28 Aug – 2 Sept
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
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
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
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
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 Portland
Renovated 1 BR Downtown Apt w/backyard
1 bedroom, 1 queen bed, 1 bathroom
31 Oct – 5 Nov
4.91 out of 5 average rating, 447 reviews
Guest favourite
Home in Portland
Island Getaway, Short ferry ride to Portland
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 23 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
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, 218 reviews
Top guest favourite
Room in Freeport
Freeport, Maine
1 queen bed, 1 bathroom
24–29 Oct
4.96 out of 5 average rating, 276 reviews
Superhost
Home in Harpswell
The Beach Pea - Waterfront cottage, Pet Friendly!
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
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
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
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
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds, 1 bathroom
1–6 Aug