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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

20–25 Sept

$4,876 SGD for 5 nights

,

4.9 out of 5 average rating, 273 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

4.95 out of 5 average rating, 80 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

$5,218 SGD for 5 nights

4.97 out of 5 average rating, 131 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

4.95 out of 5 average rating, 44 reviews

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Top guest favourite

Home in Shelter Island Heights

Laid Back Relaxation

3 bedrooms, 4 beds, 2 bathrooms

18–23 Sept

5.0 out of 5 average rating, 23 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

20–25 Sept

5.0 out of 5 average rating, 11 reviews

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Guest favourite

Home in Shelter Island Heights

Luxury Resort Style Pool Oasis, Walk To Beach

3 bedrooms, 3 beds, 2 bathrooms

18–23 Sept

5.0 out of 5 average rating, 23 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

20–25 Sept

5.0 out of 5 average rating, 77 reviews

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Guest favourite

Home in Shelter Island

Waterfront Treehouse with Pool as seen on HBO

4 bedrooms, 4 beds, 3 bathrooms

27 Sept – 2 Oct

$7,659 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews

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Top guest favourite

Home in Greenport

Greenport Beachfront Home | Private Beach & Sunset

4 bedrooms, 7 beds, 2 bathrooms

18–23 Sept

5.0 out of 5 average rating, 8 reviews

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Flat in Shelter Island Heights

5 star Waterfront cottage at Dering Harbor Inn.

1 bedroom, 3 beds, 1 bathroom

20–25 Sept

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

Free cancellation

4.91 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

4.8 out of 5 average rating, 5 reviews

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Top guest favourite

Home in Shelter Island

Shelter island retreat

2 bedrooms, 2 king beds, 1 bathroom

20–25 Sept

$3,547 SGD for 5 nights

4.97 out of 5 average rating, 172 reviews

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Guest favourite

Guest house in Shelter Island

Modern Waterfront Cottage Oasis

1 bedroom, 2 beds, 1 bathroom

20–25 Sept

$6,070 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

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Home in Shelter Island

Waterfront Retreat | Spa Pool, Sauna & Dock

3 bedrooms, 3 beds, 3.5 bathrooms

21–26 Sept

New place to stay

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Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds, 2 bathrooms

5–10 Oct

4.93 out of 5 average rating, 88 reviews

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Guest favourite

Home in Greenport

Corwin House

4 bedrooms, 4 beds, 3 bathrooms

12–18 Oct

$6,440 SGD for 6 nights

4.99 out of 5 average rating, 68 reviews

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Guest favourite

Flat in Greenport

Harbor Heights

2 bedrooms, 3 beds, 1 bathroom

15–20 Nov

$844 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 247 reviews