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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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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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Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 45 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 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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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 Cutchogue
Just renovated! North Fork life: pool, beach, wine
Individual host
26 Sept – 2 Oct
5.0 out of 5 average rating, 25 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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Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
5–10 Oct
5.0 out of 5 average rating, 3 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
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 bathrooms
21–28 Sept
5.0 out of 5 average rating, 14 reviews
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Home in Shelter Island Heights
Spacious beach house with stunning water views.
5 bedrooms, 8 beds, 4 bathrooms
4–11 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
10–15 Nov
4.99 out of 5 average rating, 105 reviews
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Top guest favourite
Home in Sag Harbor
Brick Kiln
4 bedrooms, 4 beds, 3.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 18 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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Top guest favourite
Home in Southold
Country Beach Home!
4 bedrooms, 8 beds, 2.5 bathrooms
6–11 Oct
4.96 out of 5 average rating, 24 reviews
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Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 131 reviews
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Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds, 2.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 19 reviews