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Search results; Over 1,000 homes in Southold

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Home in Southold

The Shorecrest Beach House

4 bedrooms, 6 beds, 2 private bathrooms

19–24 Oct

$5,296 SGD for 5 nights

,

5.0 out of 5 average rating, 4 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

East Hampton Beach House | Private Beach

4 bedrooms, 5 beds, 3 bathrooms

20–25 Sept

$4,466 SGD for 5 nights

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

Free cancellation

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

19–24 Sept

5.0 out of 5 average rating, 8 reviews

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Home in Water Mill

Cozy 5-Bed House in The Hamptons, NY

4 bedrooms, 5 beds, 4 bathrooms

21–26 Sept

$4,118 SGD for 5 nights

New place to stay

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Guest favourite

Home in Orient

Luxury Escape - Saltwater Pool

4 bedrooms, 7 beds, 2.5 bathrooms

20–25 Sept

$5,314 SGD for 5 nights

5.0 out of 5 average rating, 19 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

$6,266 SGD for 5 nights

4.95 out of 5 average rating, 44 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

$9,512 SGD for 5 nights

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

Rooms in Greenport

Chestnut View Room own private bathroom

2 bedrooms, 3 queen beds, No bathroom

10–15 Nov

$2,170 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 104 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

$11,643 SGD for 5 nights

4.99 out of 5 average rating, 148 reviews

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Guest favourite

Home in Southampton

Vogue Editors Home, Featured Hamptons Mag, Elle D.

4 bedrooms, 4 beds, 7.5 bathrooms

11–16 Oct

5.0 out of 5 average rating, 6 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

$7,838 SGD for 5 nights

4.89 out of 5 average rating, 9 reviews

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Top guest favourite

Home in Clinton

The Connecticut Cottage | Historic Modern Charm

2 bedrooms, 2 beds, 2 bathrooms

30 Sept – 5 Oct

$1,886 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 31 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

Free cancellation

New place to stay

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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

$3,048 SGD for 5 nights

4.89 out of 5 average rating, 44 reviews

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Top guest favourite

Home in Southold

Luxury by the Sea!!

3 bedrooms, 4 beds, 2.5 bathrooms

20–25 Sept

$5,984 SGD for 5 nights

4.95 out of 5 average rating, 59 reviews

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Top guest favourite

Home in Sag Harbor

Sag Harbor home away from home

2 bedrooms, 4 beds, 2 bathrooms

4–9 Oct

$3,481 SGD for 5 nights

4.98 out of 5 average rating, 237 reviews