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Search results; Over 1,000 homes in Southold

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Top guest favourite

Room in Southold

Vine + Sand Southold, NY's Newest B&B-Room 2

1 bedroom, 1 bed, 1 private bathroom

4–9 Oct

$3,955 SGD for 5 nights

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5.0 out of 5 average rating, 15 reviews

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Featured hotel

Hotel in Greenport

Oyster Estate, Classic king

1 bedroom, 1 king bed, 1 bathroom

4–9 Oct

$2,838 SGD for 5 nights

+$385 SGD Airbnb credit

New place to stay

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Home in East Hampton

East Hampton Beach House | Private Beach

4 bedrooms, 5 beds, 3 bathrooms

5–10 Oct

$3,904 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

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Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

1–6 Oct

$9,933 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 45 reviews

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Featured hotel

Hotel in Bridgehampton

A Room at the Beach, Bay twin room

1 bedroom, 2 single beds, 1 bathroom

4–9 Oct

$2,106 SGD for 5 nights

+$315 SGD Airbnb credit

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Home in East Hampton

Remarkable East Hampton Getaway with Pool

3 bedrooms, 3 beds, 3 bathrooms

1–6 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

$11,678 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, 7 reviews

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Guest favourite

Home in Orient

Luxury Escape - Saltwater Pool

4 bedrooms, 7 beds, 2.5 bathrooms

1–6 Oct

$4,909 SGD for 5 nights

5.0 out of 5 average rating, 19 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

$9,541 SGD for 5 nights

4.96 out of 5 average rating, 27 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

$3,058 SGD for 5 nights

4.89 out of 5 average rating, 44 reviews

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Luxe

Home in Montauk

Montauk modern 7-bedroom Heated Pool & hot tub

7 bedrooms, 10 beds, 5 bathrooms

1–6 Nov

$8,960 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 42 reviews

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Home in Shelter Island

Waterfront Retreat | Spa Pool, Sauna & Dock

3 bedrooms, 3 beds, 3.5 bathrooms

1–6 Oct

New place to stay

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Home in Cutchogue

Steps to Beach, Vineyards, Farm Stands & Village

3 bedrooms, 3 beds, 2 bathrooms

1–6 Oct

5.0 out of 5 average rating, 3 reviews

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Top guest favourite

Home in Old Saybrook

Best of both worlds!

3 bedrooms, 4 beds, 2 bathrooms

12–17 Oct

$2,016 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 119 reviews

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Top guest favourite

Home in Montauk

Oceanfront Home Downtown Montauk

3 bedrooms, 6 beds, 1.5 bathrooms

25–30 Oct

4.91 out of 5 average rating, 35 reviews

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Home in Shelter Island

NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT

5 bedrooms, 8 beds, 4.5 bathrooms

1–8 Oct

$28,094 SGD for 7 nights

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Top guest favourite

Home in East Marion

Bohemian Old Life Saving Station with Beach & Pool

6 bedrooms, 8 beds, 4 bathrooms

4–9 Oct

$8,671 SGD for 5 nights

4.97 out of 5 average rating, 114 reviews

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Superhost

Home in East Marion

Bungalow by the Bay

2 bedrooms, 2 queen beds, 1.5 bathrooms

1–6 Oct

5.0 out of 5 average rating, 4 reviews