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Search results; Over 1,000 homes in Southport

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Cottage in Southport
Water's Edge - Peaceful Waterfront Cottage!
2 bedrooms, 6 beds, 2 private bathrooms
18–25 Sept
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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, 47 reviews
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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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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, 30 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, 21 reviews
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Guest favourite
Home in Southport
Maine Carriage House
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Sept
4.97 out of 5 average rating, 30 reviews
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Guest favourite
Home in Southport
Architectural gem near Botanical Gardens
4 bedrooms, 9 beds, 3.5 bathrooms
23–28 Sept
4.92 out of 5 average rating, 50 reviews
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Top guest favourite
Cottage in Southport
Classic Cottage on Southport Island
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 50 reviews
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Guest favourite
Home in Southport
Maine Cottage/Your Year-Round Destination
4 bedrooms, 5 beds, 3 bathrooms
17–23 Sept
4.93 out of 5 average rating, 107 reviews
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Home in Boothbay Harbor
Boothbay Harbor- perfect for your Maine vacation!
5 bedrooms, 8 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Cottage in Southport
Seawood Sunset Cottage: Woods, near Beach
2 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Home in Southport
Salty Dog Cottage by Sea Maine
3 bedrooms, 6 beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Southport
The Landing: Relaxing Family Coastal Retreat
5 bedrooms, 6 beds, 2 bathrooms
17–22 Sept
4.88 out of 5 average rating, 8 reviews
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Guest favourite
Home in Boothbay Harbor
Lobster Cove Retreat
3 bedrooms, 3 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Georgetown
Five Islands Waterfront Retreat
3 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 31 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
24–29 Oct
4.98 out of 5 average rating, 287 reviews
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Top guest favourite
Home in Boothbay Harbor
The Rowe House
2 bedrooms, 2 queen beds, 1 bathroom
29 Sept – 4 Oct
4.97 out of 5 average rating, 120 reviews
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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
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Top guest favourite
Flat in Boothbay Harbor
Harbor for Two
1 bed, 1 bathroom
29 Oct – 3 Nov
5.0 out of 5 average rating, 151 reviews