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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

$5,785 SGD for 5 nights

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4.9 out of 5 average rating, 127 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

9–14 Aug

$10,351 SGD for 5 nights

4.95 out of 5 average rating, 37 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

12–17 Jul

4.97 out of 5 average rating, 118 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds, 2 bathrooms

23–30 Aug

$6,030 SGD for 7 nights

5.0 out of 5 average rating, 23 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds, 2 bathrooms

13–18 Jul

$6,850 SGD for 5 nights

4.93 out of 5 average rating, 83 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

5–10 Jul

$12,939 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Place to stay in Shelter Island

Casual Island Getaway - Walk to the Beach

1 bedroom, 1 queen bed, 1 bathroom

1–6 Sept

$1,523 SGD for 5 nights

4.91 out of 5 average rating, 137 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

13–20 Jul

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

23–28 Jul

$7,079 SGD for 5 nights

4.91 out of 5 average rating, 92 reviews

Guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$6,242 SGD for 5 nights

4.94 out of 5 average rating, 72 reviews

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds, 1 bathroom

13–18 Sept

$3,532 SGD for 5 nights

4.84 out of 5 average rating, 74 reviews

Top guest favourite

Cottage in Shelter Island

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds, 2 bathrooms

30 Aug – 4 Sept

$7,006 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews

Top guest favourite

Home in Shelter Island

CASA GYPSEA - a chic and peaceful 3 bedroom house

3 bedrooms, 3 beds, 2 bathrooms

25 Jul – 1 Aug

5.0 out of 5 average rating, 73 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Oasis Steps to Water - Heated Pool

6 bedrooms, 9 beds, 3 bathrooms

23–28 Aug

$11,990 SGD for 5 nights

5.0 out of 5 average rating, 39 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

1–6 Aug

$5,975 SGD for 5 nights

4.92 out of 5 average rating, 12 reviews

Top guest favourite

Rooms in Shelter Island

Grace House

2 bedrooms, 2 beds, 1 bathroom

13–18 Sept

$2,398 SGD for 5 nights

5.0 out of 5 average rating, 48 reviews

Guest favourite

Room in Shelter Island

Magnolia Cape with private entrance & private bath

1 king bed, 1 bathroom

5–10 Jul

$1,751 SGD for 5 nights

4.83 out of 5 average rating, 41 reviews

Guest favourite

Home in Shelter Island

Hamptons - Shelter Island Farmhouse

4 bedrooms, 4 beds, 2 bathrooms

5–10 Oct

$5,557 SGD for 5 nights

4.94 out of 5 average rating, 51 reviews

Top guest favourite

Home in Shelter Island

Private Hay Beach Retreat with Heated Pool

4 bedrooms, 5 beds, 3 bathrooms

3–10 Aug

$13,183 SGD for 7 nights

4.98 out of 5 average rating, 92 reviews