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Search results; Over 1,000 homes in Shelter Island

Guest favourite

Home in Shelter Island

Hay Beach Family Home: Fire Pit, Playroom, Yard

3 bedrooms, 4 beds, 2 private bathrooms

19–24 Jul

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4.9 out of 5 average rating, 128 reviews

Top guest favourite

Place to stay in Shelter Island

Casual Island Getaway - Walk to the Beach

1 bedroom, 1 queen bed

4–9 Oct

$1,187 SGD for 5 nights

4.91 out of 5 average rating, 140 reviews

Guest favourite

Room in Shelter Island

Magnolia Cape with private entrance & private bath

1 king bed

16–21 Jul

$1,706 SGD for 5 nights

4.83 out of 5 average rating, 42 reviews

Guest favourite

Room in Shelter Island

A room in a sunny cottage with use of pool.

1 king bed

29 Sept – 4 Oct

$1,898 SGD for 5 nights

4.95 out of 5 average rating, 146 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds

11–16 Jul

$12,803 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds

9–14 Aug

$10,091 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 38 reviews

Top guest favourite

Room in Shelter Island

Master Suite at RedHouse

1 king bed

15–20 Jul

$1,608 SGD for 5 nights

4.95 out of 5 average rating, 165 reviews

Top guest favourite

Guest suite in Shelter Island

Chic and Cozy Suite with Private Entrance

1 bedroom, 1 bed

26–31 Jul

$2,072 SGD for 5 nights

5.0 out of 5 average rating, 51 reviews

Guest favourite

Home in Shelter Island

Shelter Island 4 bed waterfront home with office

4 bedrooms, 5 beds

27 Aug – 1 Sept

$11,813 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds

23–28 Jul

$7,088 SGD for 5 nights

4.91 out of 5 average rating, 93 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds

13–20 Jul

Free cancellation

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds

2–7 Aug

$5,441 SGD for 5 nights

4.97 out of 5 average rating, 118 reviews

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds

13–18 Sept

$3,537 SGD for 5 nights

4.84 out of 5 average rating, 75 reviews

Guest favourite

Cottage in Shelter Island

Charming Coastal Cottage

3 bedrooms, 3 beds

12–17 Jul

$6,478 SGD for 5 nights

Free cancellation

4.84 out of 5 average rating, 45 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds

13–18 Jul

$6,859 SGD for 5 nights

4.93 out of 5 average rating, 84 reviews

Guest favourite

Rooms in Shelter Island

Room in Charming Coastal Cottage

2 bedrooms, 1 bed

19–24 Jul

$1,197 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 26 reviews

Top guest favourite

Home in Shelter Island

CASA GYPSEA - a chic and peaceful 3 bedroom house

3 bedrooms, 3 beds

20–27 Sept

$5,200 SGD for 7 nights

5.0 out of 5 average rating, 74 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds

3–8 Aug

$5,983 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Guest favourite

Room in Shelter Island

Candlelite Inn Queen Onsuite Bath

1 queen bed

19–24 Jul

$2,401 SGD for 5 nights

4.91 out of 5 average rating, 46 reviews