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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

$5,791 SGD for 5 nights

,

4.9 out of 5 average rating, 126 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds

6–11 Sept

$10,363 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 37 reviews

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds

23–28 Jul

$7,086 SGD for 5 nights

4.91 out of 5 average rating, 92 reviews

Top guest favourite

Place to stay in Shelter Island

Casual Island Getaway - Walk to the Beach

1 bedroom, 1 queen bed

1–6 Sept

$1,524 SGD for 5 nights

4.91 out of 5 average rating, 137 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds

12–17 Jul

4.97 out of 5 average rating, 118 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds

5–10 Jul

$12,953 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds

13–18 Jul

$6,858 SGD for 5 nights

4.93 out of 5 average rating, 83 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds

23–30 Aug

$6,037 SGD for 7 nights

5.0 out of 5 average rating, 23 reviews

Top guest favourite

Cottage in Shelter Island

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds

30 Aug – 4 Sept

$7,014 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds

13–20 Jul

Pay $0 today

Free cancellation

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds

13–18 Sept

$3,536 SGD for 5 nights

4.84 out of 5 average rating, 74 reviews

Guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds

4–9 Oct

$6,248 SGD for 5 nights

4.94 out of 5 average rating, 72 reviews

Guest favourite

Home in Shelter Island

Stunning water views, huge pool, family resort

4 bedrooms, 6 beds

16–21 Jul

$11,125 SGD for 5 nights

4.93 out of 5 average rating, 56 reviews

Top guest favourite

Rooms in Shelter Island

Grace House

2 bedrooms, 2 beds

13–18 Sept

$2,401 SGD for 5 nights

5.0 out of 5 average rating, 48 reviews

Top guest favourite

Home in Shelter Island

CASA GYPSEA - a chic and peaceful 3 bedroom house

3 bedrooms, 3 beds

25 Jul – 1 Aug

5.0 out of 5 average rating, 73 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds

1–6 Aug

$5,982 SGD for 5 nights

Pay $0 today

Free cancellation

4.92 out of 5 average rating, 12 reviews

Guest favourite

Room in Shelter Island

Magnolia Cape with private entrance & private bath

1 king bed

5–10 Jul

$1,753 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

5–10 Oct

$5,563 SGD for 5 nights

4.94 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

10–15 Jul

5.0 out of 5 average rating, 28 reviews