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Search results; Over 1,000 homes in Shelter Island Heights

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Superhost

Flat in Shelter Island Heights

Squire Chase House

3 bedrooms, 3 beds, 2 bathrooms

1–6 Dec

$4,883 SGD for 5 nights

,

4.9 out of 5 average rating, 273 reviews

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Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

1–6 Oct

$3,562 SGD for 5 nights

4.97 out of 5 average rating, 131 reviews

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Top guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$5,793 SGD for 5 nights

4.95 out of 5 average rating, 80 reviews

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Featured hotel

Hotel in Greenport

Oyster Estate, Signature King

1 bedroom, 1 king bed, 1 bathroom

1–6 Oct

$3,917 SGD for 5 nights

+$532 SGD Airbnb credit

New place to stay

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Top guest favourite

Home in Greenport

Bayview house with salt water pool & private chef

3 bedrooms, 4 beds, 2 bathrooms

4–9 Oct

$3,161 SGD for 5 nights

Free cancellation

4.91 out of 5 average rating, 22 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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Top guest favourite

Room in Shelter Island

Casual Island Getaway - Walk to the Beach

1 queen bed, 1 bathroom

4–9 Oct

$1,140 SGD for 5 nights

4.93 out of 5 average rating, 162 reviews

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Guest favourite

Home in Greenport

North Fork Sound Front Home with Pool

4 bedrooms, 4 beds, 4 bathrooms

1–6 Oct

$6,452 SGD for 5 nights

4.87 out of 5 average rating, 46 reviews

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Top guest favourite

Home in Shelter Island

Shelter Island home with pool

4 bedrooms, 6 beds, 2.5 bathrooms

19–24 Oct

$5,312 SGD for 5 nights

4.96 out of 5 average rating, 74 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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Guest favourite

Guest house in Shelter Island

Modern Waterfront Cottage Oasis

1 bedroom, 2 beds, 1 bathroom

1–6 Oct

$4,800 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 10 reviews

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Home in Greenport

Brand New Build! Greenport Gem w/ Yard & Patio

3 bedrooms, 3 beds, 3.5 bathrooms

12–17 Oct

$3,014 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

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Flat in Shelter Island Heights

5 star Waterfront cottage at Dering Harbor Inn.

1 bedroom, 3 beds, 1 bathroom

1–6 Oct

New place to stay

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Guest favourite

Home in Greenport

Charming Greenport Escape – Walk to Town & Beaches

4 bedrooms, 5 beds, 2 bathrooms

1–6 Oct

$4,092 SGD for 5 nights

5.0 out of 5 average rating, 22 reviews

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Home in Shelter Island

Shelter Island House with water views & cottage

5 bedrooms, 6 beds, 3 bathrooms

2–7 Oct

$3,994 SGD for 5 nights

4.8 out of 5 average rating, 5 reviews

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Top guest favourite

Home in Greenport

Cosy North Fork Cottage with large backyard

3 bedrooms, 3 beds, 2 bathrooms

8–13 Nov

$2,624 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 167 reviews

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Top guest favourite

Home in Shelter Island

CASA GYPSEA - a chic and peaceful 3 bedroom house

3 bedrooms, 3 beds, 2 bathrooms

1–6 Oct

$3,331 SGD for 5 nights

5.0 out of 5 average rating, 77 reviews

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Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

15–22 Sept

$7,240 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

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Top guest favourite

Home in Shelter Island

Shelter Island 4 BR w Pool & Private Beach Access

4 bedrooms, 7 beds, 2 bathrooms

1–6 Oct

$5,772 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews