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Search results; Over 1,000 homes in Southport

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Top guest favourite
Home in Southport
Cozy Harbor Waterfront
4 bedrooms, 5 beds
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
11–16 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Home in Southport
Southport, views of Christmas cove (Boothbay area)
3 bedrooms, 5 beds
29 Sept – 4 Oct
4.95 out of 5 average rating, 21 reviews
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Top guest favourite
Cottage in Southport
Cottage at Island Point; Charming Coastal Retreat
3 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 31 reviews
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Superhost
Home in Southport
Maine Cottage/Your Year-Round Destination
4 bedrooms, 5 beds
20–26 Sept
4.93 out of 5 average rating, 107 reviews
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Guest favourite
Home in Southport
Maine Carriage House
2 bedrooms, 2 queen beds
20–25 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
23–28 Sept
4.92 out of 5 average rating, 50 reviews
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Top guest favourite
Home in Southport
Modern home on Southport Island
3 bedrooms, 3 beds
30 May – 4 Jun
4.97 out of 5 average rating, 62 reviews
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Top guest favourite
Home in Boothbay Harbor
Boothbay Harbor- perfect for your Maine vacation!
5 bedrooms, 8 beds
19–24 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
26 Sept – 1 Oct
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Home in Southport
The Landing: Relaxing Family Coastal Retreat
5 bedrooms, 6 beds
20–25 Sept
4.88 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
28 Sept – 3 Oct
5.0 out of 5 average rating, 31 reviews
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Cottage in Southport
Stunning Ocean Front October 1-14 20% Off
3 bedrooms, 3 beds
8–13 May
5.0 out of 5 average rating, 18 reviews
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Superhost
Cottage in Southport
Stuart Little by Sea Maine
5 bedrooms, 7 beds
30 Jul – 4 Aug
4.6 out of 5 average rating, 10 reviews
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Guest favourite
Cabin in Southport
Sprucerock Cabin by Sea Maine
3 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Home in Boothbay Harbor
The Osprey - 6 Person Summer Cottage
4 bedrooms, 6 beds
26 Sept – 3 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Cabin in Boothbay Harbor
Lakeside 3 BR Cabin in Boothbay Harbor
3 bedrooms, 4 beds
24–29 Oct
4.98 out of 5 average rating, 287 reviews
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Superhost
Home in Boothbay
Greyview Cottage on Ocean Point | Sleeps 6
3 bedrooms, 4 beds
20–25 Sept