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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
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
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
Home in Portland
Historic Island Retreat
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
Top guest favourite
Tiny home in Portland
The Garden Cabin Tiny Home
1 bedroom, 1 double bed, 1.5 bathrooms
1–6 Dec
4.95 out of 5 average rating, 552 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
Top guest favourite
Home in Georgetown
Cottage on Todd Bay
3 bedrooms, 4 beds, 1.5 bathrooms
5–10 Oct
4.98 out of 5 average rating, 151 reviews
Top guest favourite
Flat in Phippsburg
Twin Heart Treetop
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Guest house in Freeport
Cozy Maine Barn Hideaway- 2nd Floor Guesthouse
2 bedrooms, 2 beds, 1 bathroom
20–25 Oct
5.0 out of 5 average rating, 242 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
Top guest favourite
Rooms in Brunswick
Coastal guest suite for oyster lovers
2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
5.0 out of 5 average rating, 114 reviews
Home in Wells
GG's Cabin in the Woods
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Tiny home in Durham
Crow’s Nest Tiny House at Old Crow Ranch
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 394 reviews
Top guest favourite
Home in Wiscasset
Cozy Midcoast Island Cottage
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
Guest favourite
Loft in Harpswell
Oceanfront Studio w/ Private Dock in Harpswell!
1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Falmouth
The little blue cottage
2 beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Room in Biddeford
King Bedroom at Thistle Pond. Close to UNE & Beach
1 king bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 72 reviews
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
2 bedrooms, 2 queen beds, 1.5 bathrooms
22–27 Sept