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Search results; Over 1,000 homes in Southport

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Top guest favourite
Cottage in Southport
Cottage at Island Point; Charming Coastal Retreat
3 bedrooms, 5 beds, 2 shared bathrooms
27 Sept – 2 Oct
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5.0 out of 5 average rating, 27 reviews
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Home in Southport
Maine Cottage/Your Year-Round Destination
4 bedrooms, 5 beds, 3 bathrooms
1–7 Sept
4.92 out of 5 average rating, 106 reviews
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Home in Southport
The Landing: Relaxing Family Coastal Retreat
5 bedrooms, 6 beds, 2 bathrooms
1–6 Sept
4.86 out of 5 average rating, 7 reviews
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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, 19 reviews
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Home in Georgetown
Bay View on Blueberry Hill
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.94 out of 5 average rating, 16 reviews
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Flat in Southport
Boothbay Region Woods & Water Retreat on Southport
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.83 out of 5 average rating, 29 reviews
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Home in Southport
Maine Carriage House
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Sept
4.96 out of 5 average rating, 28 reviews
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Cottage in Southport
Stuart Little by Sea Maine
5 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
4.6 out of 5 average rating, 10 reviews
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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, 34 reviews
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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, 48 reviews
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Home in Southport
Architectural gem near Botanical Gardens
4 bedrooms, 9 beds, 3.5 bathrooms
8–13 Sept
4.92 out of 5 average rating, 48 reviews
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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
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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, 106 reviews
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Top guest favourite
Home in Boothbay Harbor
Boothbay Harbor- perfect for your Maine vacation!
5 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 22 reviews
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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, 22 reviews
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Top guest favourite
Cabin in Boothbay Harbor
Lakeside 3 BR Cabin in Boothbay Harbor
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 284 reviews
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Cabin in Boothbay Harbor
Sebasco Sprucewold Cabin@ the Beach
1 bedroom, 1 queen bed, 1 bathroom
8–13 Dec
4.88 out of 5 average rating, 138 reviews
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Home in Boothbay Harbor
Peace by the ocean
3 bedrooms, 6 beds, 2 bathrooms
12–17 Sept
4.95 out of 5 average rating, 19 reviews
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Home in Georgetown
Quintessential Maine Waterfront Home
3 bedrooms, 3 queen beds, 3 bathrooms
20–25 Sept
4.9 out of 5 average rating, 10 reviews