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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
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
Superhost
Home in Chebeague Island
Post & beam house on three wooded acres
2 bedrooms, 4 beds, 1 bathroom
17–22 Aug
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
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
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
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 queen beds, 1.5 bathrooms
28 Aug – 2 Sept
Top guest favourite
Cottage in Pownal
Dreamy Post&Beam Hideaway Near Portland & Freeport
1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
4.99 out of 5 average rating, 470 reviews
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
Home in Yarmouth
Peaceful retreat in Yarmouth
2 bedrooms, 2 double beds, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Tiny home in Freeport
The Craic House Maine #mainethewaylifeshouldbe
1 bedroom, 1 king bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds, 1 bathroom
28 Oct – 2 Nov
5.0 out of 5 average rating, 12 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, 6 reviews
Top guest favourite
Home in Falmouth
The little blue cottage
2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 9 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
Guest favourite
Cabin in Freeport
Modern woods cabin w/ full bath & kitchen - 01
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 73 reviews
Top guest favourite
Tiny home in Scarborough
Cozy Tiny Cottage • 9mi Portland • 6mi Beach
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.98 out of 5 average rating, 128 reviews