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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

$3,764 SGD for 5 nights

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5.0 out of 5 average rating, 22 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

Home in Shelter Island

Waterfront Retreat | Spa Pool, Sauna & Dock

3 bedrooms, 3 beds, 3.5 bathrooms

8–13 Sept

$8,713 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

$5,199 SGD for 5 nights

4.97 out of 5 average rating, 129 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

Guest favourite

Home in Shelter Island

Mid-Century Gem with Pool. Steps to Private Beach.

3 bedrooms, 3 beds, 2.5 bathrooms

7–14 Sept

$13,023 SGD for 7 nights

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$5,995 SGD for 5 nights

4.95 out of 5 average rating, 79 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat | 3 King Beds + Huge Yard

4 bedrooms, 5 beds, 2.5 bathrooms

8–13 Sept

$7,014 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in Shelter Island

Shelter Island Home with Large Yard And Pool

3 bedrooms, 6 beds, 2 bathrooms

9–16 Sept

$6,543 SGD for 7 nights

5.0 out of 5 average rating, 13 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

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

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

2–7 Sept

5.0 out of 5 average rating, 10 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds, 2 bathrooms

17–22 Apr

$5,071 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 26 reviews

Guest favourite

Flat in Greenport

Harbor Heights

2 bedrooms, 3 beds, 1 bathroom

1–6 Nov

$871 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 247 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

$7,835 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews

Guest favourite

Home in Shelter Island Heights

Luxury Resort Style Pool Oasis, Walk To Beach

3 bedrooms, 3 beds, 2 bathrooms

7–12 Sept

5.0 out of 5 average rating, 21 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

$9,204 SGD for 5 nights

4.91 out of 5 average rating, 90 reviews

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

Guest favourite

Home in Greenport

Bayview house with salt water pool & private chef

3 bedrooms, 4 beds, 2 bathrooms

4–9 Oct

$3,669 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 18 reviews