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

Guest favourite

Room in Shelter Island Heights

SEVEN on Shelter - Queen Room w/Private Bathroom

1 bedroom, 1 bed, 1 shared bathroom

30 Aug – 4 Sept

$4,369 SGD for 5 nights

,

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$10,001 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 41 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

5–12 Aug

Free cancellation

Top guest favourite

Guest house in Shelter Island

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds, 1 bathroom

4–9 Aug

$3,153 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 76 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds, 2 bathrooms

10–15 Aug

$6,473 SGD for 5 nights

4.93 out of 5 average rating, 84 reviews

Top guest favourite

Place to stay in Shelter Island

Casual Island Getaway - Walk to the Beach

1 bedroom, 1 queen bed, 1 bathroom

4–9 Oct

$1,148 SGD for 5 nights

4.92 out of 5 average rating, 143 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

7–12 Aug

$12,609 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Home in Southold

The Shorecrest Beach House

4 bedrooms, 6 beds, 2 bathrooms

19–24 Oct

$5,349 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

6–11 Sept

$4,315 SGD for 5 nights

4.97 out of 5 average rating, 123 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

9–14 Aug

$5,963 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Guest favourite

Home in Shelter Island

Peaceful Bright Country House

3 bedrooms, 3 beds, 2 bathrooms

8–13 Sept

$4,551 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Guest favourite

Home in Greenport

The Greenport Bungalow

3 bedrooms, 3 beds, 2 bathrooms

21–26 Sept

4.97 out of 5 average rating, 294 reviews

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

14–19 Aug

$7,327 SGD for 5 nights

4.92 out of 5 average rating, 95 reviews

Guest favourite

Flat in Greenport

Greenport Harbor Apartment

3 bedrooms, 4 beds, 2 bathrooms

2–7 Aug

$3,791 SGD for 5 nights

4.96 out of 5 average rating, 98 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

$13,181 SGD for 7 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds, 2 bathrooms

23–30 Aug

$6,018 SGD for 7 nights

5.0 out of 5 average rating, 24 reviews

Top guest favourite

Home in Greenport

Beach House in L.I. Wine Country

3 bedrooms, 4 beds, 2 bathrooms

31 Aug – 5 Sept

4.98 out of 5 average rating, 122 reviews

Top guest favourite

Home in Greenport

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

3 bedrooms, 3 beds, 2 bathrooms

8–13 Sept

$4,095 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 55 reviews

Top guest favourite

Room in Shelter Island

Master Suite at RedHouse

1 king bed, 1 bathroom

21–26 Aug

$1,634 SGD for 5 nights

4.95 out of 5 average rating, 168 reviews