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Search results; Over 1,000 homes in Southold

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Top guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 44 reviews
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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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Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds, 3.5 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 70 reviews
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Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 30 reviews
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Top guest favourite
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
3 bedrooms, 3 beds, 2 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 171 reviews
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Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Oct
4.98 out of 5 average rating, 171 reviews
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Top guest favourite
Home in East Hampton
Amagansett Farmhouse Retreat - Pool Through Oct.
4 bedrooms, 6 beds, 3 bathrooms
29 Sept – 4 Oct
4.99 out of 5 average rating, 111 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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Home in East Hampton
East Hamptons Modern 8 Bedroom New Construction
8 bedrooms, 8 beds, 6 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 169 reviews
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Top guest favourite
Home in East Hampton
Designer East Hampton with Bay Views + Pool
4 bedrooms, 4 beds, 3.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 31 reviews
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Guest favourite
Home in Old Saybrook
Old Saybrook on the Oyster River
5 bedrooms, 6 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 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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Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 5 beds, 3 bathrooms
23–28 Sept
New place to stay
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Home in Wainscott
Private, Charming, Lovely Farmhouse, 1 mi to ocean
3 bedrooms, 4 beds, 3 bathrooms
19–24 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 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