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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

$3,944 SGD for 5 nights

,

5.0 out of 5 average rating, 14 reviews

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Home in East Hampton

Remarkable East Hampton Getaway with Pool

3 bedrooms, 3 beds, 3 bathrooms

1–6 Oct

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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

$11,644 SGD for 5 nights

4.99 out of 5 average rating, 148 reviews

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Home in Water Mill

Cozy 5-Bed House in The Hamptons, NY

4 bedrooms, 5 beds, 4 bathrooms

1–6 Oct

$4,231 SGD for 5 nights

Free cancellation

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

$3,893 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

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Guest favourite

Home in Orient

Luxury Escape - Saltwater Pool

4 bedrooms, 7 beds, 2.5 bathrooms

1–6 Oct

$4,735 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

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Guest favourite

Holiday home in Orient

Private Vineyard w/Pool, Walk to Beach & Village

3 bedrooms, 4 beds, 3 bathrooms

1–6 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

$9,513 SGD for 5 nights

4.96 out of 5 average rating, 27 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

$9,903 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 45 reviews

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Guest favourite

Home in East Marion

Waterfront 3BR Home w/Private Beach on Peconic Bay

3 bedrooms, 4 beds, 2 bathrooms

1–8 Oct

Weekly discount

4.89 out of 5 average rating, 44 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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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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Luxe

Home in Montauk

Montauk modern 7-bedroom Heated Pool & hot tub

7 bedrooms, 10 beds, 5 bathrooms

25–30 Oct

Free cancellation

5.0 out of 5 average rating, 40 reviews

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Luxe

Villa in East Hampton

Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess

3 bedrooms, 3 beds, 3.5 bathrooms

1–6 Oct

$7,387 SGD for 5 nights

4.99 out of 5 average rating, 70 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

$3,048 SGD for 5 nights

4.89 out of 5 average rating, 44 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

Free cancellation

New place to stay

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Top guest favourite

Home in Sagaponack

Amazing Home close to Everything -

5 bedrooms, 7 beds, 4 bathrooms

4–9 Oct

$1,981 SGD for 5 nights

4.94 out of 5 average rating, 334 reviews

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Bungalow in Old Lyme

Your Coastal Getaway Awaits in Old Lyme, CT!

3 bedrooms, 3 queen beds, 1.5 bathrooms

4–9 Oct

New place to stay

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Top guest favourite

Home in Sag Harbor

Sag Harbor Village Gem

3 bedrooms, 3 beds, 2.5 bathrooms

1–6 Oct

5.0 out of 5 average rating, 102 reviews