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Search results; Over 1,000 homes in Southport

Cottage in Southport
Classic Boathouse - Waterfront Cottage + Dock!
2 bedrooms, 4 beds, 1 shared bathroom
20–27 Sept
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Top guest favourite
Cottage in Southport
Classic Cottage on Southport Island
2 bedrooms, 2 beds, 1.5 bathrooms
6–11 Sept
4.96 out of 5 average rating, 49 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, 20 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 Georgetown
Bay View on Blueberry Hill
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.94 out of 5 average rating, 16 reviews
Home in Boothbay Harbor
"Best of Maine" Oceanfront Cottage 5 STARS
1 bedroom, 2 beds, 1 bathroom
21–26 Nov
4.69 out of 5 average rating, 121 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
Top guest favourite
Flat in Boothbay Harbor
Deckhouse with Footbridge Views!
1 bedroom, 1 queen bed, 1 bathroom
21–26 Oct
4.96 out of 5 average rating, 427 reviews
Guest favourite
Flat in Southport
Boothbay Region Woods & Water Retreat on Southport
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.83 out of 5 average rating, 29 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
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, 65 reviews
Top guest favourite
Cottage in Southport
Seawood Sunset Cottage: Woods, near Beach
2 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 23 reviews
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
Top guest favourite
Home in Boothbay Harbor
Quiet Oasis Family Home Close to East Side of Town
3 bedrooms, 4 beds, 3 bathrooms
9–14 Sept
4.93 out of 5 average rating, 46 reviews
Home in Boothbay
Historic Kenniston Hill House Boothbay, Maine
4 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Boothbay Harbor
Harborfields Lodge on the Shore Boothbay
6 bedrooms, 7 beds, 3 bathrooms
9–14 Sept
4.86 out of 5 average rating, 14 reviews
Guest favourite
Home in Boothbay Harbor
Oceanfront Retreat +Dock: In L. L. Bean Catalog
5 bedrooms, 10 beds, 4 bathrooms
1–8 Oct
4.91 out of 5 average rating, 35 reviews
Top guest favourite
Guest suite in Boothbay
Linekin Guest Suite
1 bedroom, 2 beds, 1 bathroom
12–17 Oct
4.96 out of 5 average rating, 186 reviews