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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

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5.0 out of 5 average rating, 22 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

6–11 Sept

$4,252 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

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$9,462 SGD for 5 nights

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

$8,243 SGD for 5 nights

New place to stay

Top guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$5,971 SGD for 5 nights

4.95 out of 5 average rating, 79 reviews

Guest favourite

Home in Greenport

Cosy North Fork Cottage with large backyard

3 bedrooms, 3 beds, 2 bathrooms

1–6 Nov

$2,549 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 163 reviews

Guest favourite

Flat in Greenport

Harbor Heights

2 bedrooms, 3 beds, 1 bathroom

1–6 Nov

$867 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

$7,803 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews

Home in Shelter Island

NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT

5 bedrooms, 8 beds, 4.5 bathrooms

30 Sept – 7 Oct

$32,810 SGD for 7 nights

Top guest favourite

Home in Shelter Island

Shelter Island home with pool

4 bedrooms, 6 beds, 2.5 bathrooms

5–10 Oct

$6,951 SGD for 5 nights

4.96 out of 5 average rating, 71 reviews

Guest favourite

Home in Greenport

Bayview house with salt water pool & private chef

3 bedrooms, 4 beds, 2 bathrooms

4–9 Oct

$3,654 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 19 reviews

Home in Greenport

Brand New Build! Greenport Gem w/ Yard & Patio

3 bedrooms, 3 beds, 3.5 bathrooms

12–17 Sept

New place to stay

Guest favourite

Home in Shelter Island

Shelter Island Home with Large Yard And Pool

3 bedrooms, 6 beds, 2 bathrooms

9–16 Sept

5.0 out of 5 average rating, 13 reviews

Guest favourite

Home in Greenport

North Fork Sound Front Home with Pool

4 bedrooms, 4 beds, 4 bathrooms

7–12 Sept

$7,139 SGD for 5 nights

4.89 out of 5 average rating, 44 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, 22 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

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

Beach House in L.I. Wine Country

3 bedrooms, 4 beds, 2 bathrooms

28 Sept – 3 Oct

4.98 out of 5 average rating, 125 reviews