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Search results; Over 1,000 homes in Southport

Guest favourite
Home in Southport
Maine Cottage/Your Year-Round Destination
4 bedrooms, 5 beds, 3 bathrooms
14–20 Sept
4.93 out of 5 average rating, 107 reviews
Guest favourite
Home in Southport
Maine Carriage House
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Home in Southport
Modern home on Southport Island
3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
4.97 out of 5 average rating, 61 reviews
Top guest favourite
Home in Boothbay Harbor
Pinkham Cove - Water Front Cottage
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 107 reviews
Guest favourite
Home in Southport
Southport, views of Christmas cove (Boothbay area)
3 bedrooms, 5 beds, 1.5 bathrooms
29 Sept – 4 Oct
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Cottage in Southport
Cottage at Island Point; Charming Coastal Retreat
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Boothbay Harbor
The Osprey - 6 Person Summer Cottage
4 bedrooms, 6 beds, 2 bathrooms
26 Sept – 3 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Cottage in Southport
Seawood Sunset Cottage: Woods, near Beach
2 bedrooms, 5 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Boothbay Harbor
The Rowe House
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Sept
4.97 out of 5 average rating, 118 reviews
Guest favourite
Home in Boothbay Harbor
Oceanfront Retreat +Dock: In L. L. Bean Catalog
5 bedrooms, 10 beds, 4 bathrooms
16–21 Sept
4.91 out of 5 average rating, 35 reviews
Guest favourite
Cottage in Southport
Little Nick by Sea Maine
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
4.85 out of 5 average rating, 66 reviews
Guest favourite
Home in Boothbay Harbor
Harborfields Lodge on the Shore Boothbay
6 bedrooms, 7 beds, 3 bathrooms
11–16 Sept
4.86 out of 5 average rating, 14 reviews
Top guest favourite
Home in Georgetown
Bay View on Blueberry Hill
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Boothbay Harbor
Spruce Ledge Home by Sea Maine
4 bedrooms, 4 queen beds, 2.5 bathrooms
21–26 Oct
5.0 out of 5 average rating, 13 reviews
Cottage in Southport
Classic Boathouse - Waterfront Cottage + Dock!
2 bedrooms, 4 beds, 1 bathroom
12–19 Sept
Home in Boothbay Harbor
Harbor View House | Walk to Water
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
New place to stay
Superhost
Home in Boothbay
Greyview Cottage on Ocean Point | Sleeps 6
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Southport
Cozy Harbor Waterfront
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Oct
4.89 out of 5 average rating, 45 reviews