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

Top guest favourite

Home in Shelter Island Heights

Laid Back Relaxation

3 bedrooms, 4 beds, 2 bathrooms

7–12 Sept

$3,758 SGD for 5 nights

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5.0 out of 5 average rating, 22 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

Free cancellation

4.95 out of 5 average rating, 43 reviews

Home in Shelter Island

Waterfront Retreat | Spa Pool, Sauna & Dock

3 bedrooms, 3 beds, 3.5 bathrooms

8–13 Sept

$8,697 SGD for 5 nights

New place to stay

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

6–11 Sept

$5,190 SGD for 5 nights

4.97 out of 5 average rating, 129 reviews

Superhost

Home in Shelter Island

Light- filled historic home -walk to water-pool

6 bedrooms, 6 beds, 4 bathrooms

7–12 Sept

Free cancellation

Top guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$5,984 SGD for 5 nights

4.95 out of 5 average rating, 79 reviews

Guest favourite

Villa in Greenport

Year-Round Heated Pool Villa - 3 blocks from town

4 bedrooms, 8 queen beds, 4.5 bathrooms

13–18 Sept

$8,972 SGD for 5 nights

4.91 out of 5 average rating, 90 reviews

Guest favourite

Home in Shelter Island

Shelter Island Home with Large Yard And Pool

3 bedrooms, 6 beds, 2 bathrooms

9–16 Sept

$6,531 SGD for 7 nights

5.0 out of 5 average rating, 13 reviews

Guest favourite

Home in Shelter Island

Waterfront Treehouse with Pool as seen on HBO

4 bedrooms, 4 beds, 3 bathrooms

27 Sept – 2 Oct

$7,821 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews

Superhost

Home in East Marion

Bungalow by the Bay

2 bedrooms, 2 queen beds, 1.5 bathrooms

28 Sept – 3 Oct

Free cancellation

Guest favourite

Home in Shelter Island

Shelter Island Retreat | 3 King Beds + Huge Yard

4 bedrooms, 5 beds, 2.5 bathrooms

8–13 Sept

$7,001 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in Greenport

Beach House in L.I. Wine Country

3 bedrooms, 4 beds, 2 bathrooms

7–12 Sept

$3,637 SGD for 5 nights

4.98 out of 5 average rating, 125 reviews

Top guest favourite

Flat in Greenport

Upscale Newly Constructed Apartment

3 bedrooms, 6 beds, 2 bathrooms

9–14 Sept

Free cancellation

4.96 out of 5 average rating, 178 reviews

Guest favourite

Home in Greenport

Aqua Vista

2 bedrooms, 3 beds, 1 bathroom

29 Oct – 3 Nov

Free cancellation

4.95 out of 5 average rating, 270 reviews

Home in Greenport

Brand New Build! Greenport Gem w/ Yard & Patio

3 bedrooms, 3 beds, 3.5 bathrooms

12–17 Sept

$3,816 SGD for 5 nights

New place to stay

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, 8 reviews

Top guest favourite

Home in Shelter Island

Chic, serene, designer home with pool and views

4 bedrooms, 5 beds, 3 bathrooms

8–13 Sept

$8,351 SGD for 5 nights

4.98 out of 5 average rating, 44 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

7–14 Sept

Free cancellation

5.0 out of 5 average rating, 3 reviews

Guest favourite

Cottage in Shelter Island

Charming Coastal Cottage

3 bedrooms, 3 beds, 1.5 bathrooms

1–6 Oct

$5,619 SGD for 5 nights

Free cancellation

4.85 out of 5 average rating, 47 reviews