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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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Top guest favourite
Home in Southport
Modern home on Southport Island
3 bedrooms, 3 beds, 3 bathrooms
6–11 Sept
4.97 out of 5 average rating, 58 reviews
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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, 19 reviews
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Home in Southport
Cozy Harbor Waterfront
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Oct
4.89 out of 5 average rating, 44 reviews
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Guest favourite
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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Top guest favourite
Home in Southport
Waterfront cottage with private dock Southport, ME
3 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 17 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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Cottage in Southport
Stunning Ocean Front October 1-14 20% Off
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 May
5.0 out of 5 average rating, 18 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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Superhost
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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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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Superhost
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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Superhost
Home in Southport
Water's Edge on Pratts Island by Sea Maine
7 bedrooms, 1 king bed, 4 bathrooms
15–20 May
5.0 out of 5 average rating, 3 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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Superhost
Home in Southport
Salty Dog Cottage by Sea Maine
3 bedrooms, 6 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 3 reviews
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Home in Boothbay Harbor
The Corner House
3 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
4.89 out of 5 average rating, 9 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
Flat in Boothbay Harbor
Harbor for Two
1 bed, 1 bathroom
28 Oct – 2 Nov
5.0 out of 5 average rating, 148 reviews