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Search results; Over 1,000 homes in Southport

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, 29 reviews
Guest favourite
Home in Southport
Maine Cottage/Your Year-Round Destination
4 bedrooms, 5 beds
14–20 Sept
4.93 out of 5 average rating, 107 reviews
Top guest favourite
Home in Southport
Cozy Harbor Waterfront
4 bedrooms, 5 beds
13–18 Oct
4.89 out of 5 average rating, 45 reviews
Top 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
Top guest favourite
Home in Southport
Modern home on Southport Island
3 bedrooms, 3 beds
8–13 Sept
4.97 out of 5 average rating, 61 reviews
Guest favourite
Home in Southport
Maine Carriage House
2 bedrooms, 2 queen beds
9–14 Sept
4.97 out of 5 average rating, 30 reviews
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
Guest favourite
Home in Southport
Architectural gem near Botanical Gardens
4 bedrooms, 9 beds
23–28 Sept
4.92 out of 5 average rating, 48 reviews
Top guest favourite
Home in Boothbay Harbor
Boothbay Harbor- perfect for your Maine vacation!
5 bedrooms, 8 beds
13–18 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Cottage in Southport
Seawood Sunset Cottage: Woods, near Beach
2 bedrooms, 5 beds
10–15 Sept
5.0 out of 5 average rating, 23 reviews
Superhost
Home in Southport
Water's Edge on Pratts Island by Sea Maine
7 bedrooms, 1 king bed
15–20 May
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Boothbay Harbor
Oceanfront Retreat +Dock: In L. L. Bean Catalog
5 bedrooms, 10 beds
1–8 Oct
4.91 out of 5 average rating, 35 reviews
Guest favourite
Home in Boothbay Harbor
Lobster Cove Retreat
3 bedrooms, 3 beds
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Boothbay Harbor
Quiet Oasis Family Home Close to East Side of Town
3 bedrooms, 4 beds
9–14 Sept
4.93 out of 5 average rating, 46 reviews
Top guest favourite
Home in Ocean Point
137 Shore Road Ocean Point view now with WiFi
2 bedrooms, 2 double beds
11–16 Sept
4.95 out of 5 average rating, 56 reviews
Superhost
Home in Southport
The Landing: Relaxing Family Coastal Retreat
5 bedrooms, 6 beds
9–14 Sept
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Georgetown
Cottage on Todd Bay
3 bedrooms, 4 beds
18–23 Oct
4.98 out of 5 average rating, 154 reviews
Guest favourite
Home in Boothbay Harbor
Welcome to 8 West!
7 bedrooms, 12 beds
4–9 Oct
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Southport
Salty Dog Cottage by Sea Maine
3 bedrooms, 6 beds
8–13 Sept
5.0 out of 5 average rating, 3 reviews