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Search results; Over 1,000 homes in Southold

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Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 bed, 1 private bathroom
3–8 Oct
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4.94 out of 5 average rating, 159 reviews
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Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct
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Home in East Hampton
Remarkable East Hampton Getaway with Pool
3 bedrooms, 3 beds, 3 bathrooms
17–22 Sept
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Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in East Hampton
Beautiful east hampton cottage by the bay
4 bedrooms, 2 queen beds, 2.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Home in Clinton
Luxury 5 BR Beachfront Retreat
5 bedrooms, 8 beds, 3 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 9 reviews
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Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds, 8.5 bathrooms
11–16 Oct
4.99 out of 5 average rating, 148 reviews
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Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Home in East Marion
New! 6BR, 4.5 Bath, Pool, Hot Tub, Walk to Beach
6 bedrooms, 8 beds, 4.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 26 reviews
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Flat in East Hampton
Charming spacious private studio in Springs
1 bedroom, 3 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Greenport
Walk to Beach or to Town …
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.88 out of 5 average rating, 43 reviews
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Superhost
Home in Old Lyme
Surf Cottage (1 Minute Walk to Private Beach)
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
New place to stay
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Luxe
Home in Montauk
Montauk modern 7-bedroom Heated Pool & hot tub
7 bedrooms, 10 beds, 5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 40 reviews
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Top guest favourite
Home in East Marion
Long Island home with pool 1 mile from Greenport
3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms, 9 beds, 3.5 bathrooms
3–8 Oct
4.96 out of 5 average rating, 27 reviews
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Top guest favourite
Home in Amagansett
Bliss by the Ocean!
6 bedrooms, 7 beds, 5.5 bathrooms
12–17 Oct
4.94 out of 5 average rating, 71 reviews
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Top guest favourite
Home in Southold
Waterfront, Dock, Boat Ramp, Hot Tub & Beaches
4 bedrooms, 8 beds, 3 bathrooms
21–26 Sept
5.0 out of 5 average rating, 6 reviews