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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

$5,799 SGD for 5 nights

,

4.9 out of 5 average rating, 126 reviews

Guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$10,377 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 35 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds, 2 bathrooms

23–30 Aug

$6,649 SGD for 7 nights

5.0 out of 5 average rating, 23 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, 117 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

$12,819 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

$1,526 SGD for 5 nights

4.91 out of 5 average rating, 136 reviews

Top guest favourite

Rooms in Shelter Island

Grace House

2 bedrooms, 2 beds, 1 bathroom

12–17 Jul

$2,179 SGD for 5 nights

5.0 out of 5 average rating, 48 reviews

Guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$6,257 SGD for 5 nights

4.94 out of 5 average rating, 72 reviews

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

23–28 Jul

$7,096 SGD for 5 nights

4.91 out of 5 average rating, 91 reviews

Top guest favourite

Cottage in Shelter Island

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds, 2 bathrooms

30 Aug – 4 Sept

$7,023 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds, 2 bathrooms

13–18 Jul

$6,867 SGD for 5 nights

4.93 out of 5 average rating, 83 reviews

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds, 1 bathroom

13–18 Sept

$3,541 SGD for 5 nights

4.84 out of 5 average rating, 73 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

13–20 Jul

Free cancellation

New place to stay

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

$9,614 SGD for 7 nights

5.0 out of 5 average rating, 73 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

1–6 Aug

$5,990 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 12 reviews

Top guest favourite

Home in Shelter Island

Private Hay Beach Retreat with Heated Pool

4 bedrooms, 5 beds, 3 bathrooms

3–10 Aug

$13,215 SGD for 7 nights

4.98 out of 5 average rating, 92 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

$12,020 SGD for 5 nights

5.0 out of 5 average rating, 38 reviews

Guest favourite

Home in Shelter Island

Hamptons - Shelter Island Farmhouse

4 bedrooms, 4 beds, 2 bathrooms

17–22 Aug

$5,036 SGD for 5 nights

4.94 out of 5 average rating, 51 reviews

Top guest favourite

Home in Shelter Island

Light, spacious 3bdr home steps to Wades Beach

3 bedrooms, 4 beds, 2.5 bathrooms

20–25 Sept

$5,204 SGD for 5 nights

4.93 out of 5 average rating, 43 reviews