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Search results; Over 1,000 homes in Shelter Island

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 private bathrooms

23–28 Jul

$7,091 SGD for 5 nights

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4.91 out of 5 average rating, 93 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

9–14 Aug

$10,369 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 37 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

$1,188 SGD for 5 nights

4.91 out of 5 average rating, 139 reviews

Home in Shelter Island

Private Shelter Island Escape | Huge Yard + Pool

4 bedrooms, 5 beds, 2.5 bathrooms

18–23 Jul

$9,240 SGD for 5 nights

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

2–7 Aug

$5,589 SGD for 5 nights

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

$6,040 SGD for 7 nights

5.0 out of 5 average rating, 23 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

10–15 Jul

$13,113 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, 2 bathrooms

13–18 Jul

$6,862 SGD for 5 nights

4.93 out of 5 average rating, 84 reviews

Top guest favourite

Cottage in Shelter Island

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds, 2 bathrooms

30 Aug – 4 Sept

$7,018 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews

Guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$6,252 SGD for 5 nights

4.95 out of 5 average rating, 74 reviews

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds, 1 bathroom

17–22 Aug

$3,889 SGD for 5 nights

4.84 out of 5 average rating, 75 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

3–8 Aug

$5,985 SGD for 5 nights

Pay $0 today

Free cancellation

4.92 out of 5 average rating, 13 reviews

Guest favourite

Home in Shelter Island

Shelter Island 4 bed waterfront home with office

4 bedrooms, 5 beds, 2.5 bathrooms

10–15 Jul

5.0 out of 5 average rating, 28 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

13–20 Jul

Pay $0 today

Free cancellation

Top guest favourite

Home in Shelter Island

CASA GYPSEA - a chic and peaceful 3 bedroom house

3 bedrooms, 3 beds, 2 bathrooms

20–27 Sept

5.0 out of 5 average rating, 73 reviews

Guest favourite

Rooms in Shelter Island

Grace House

2 bedrooms, 2 beds, 1 bathroom

13–18 Sept

$2,402 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

16–21 Jul

$1,707 SGD for 5 nights

4.83 out of 5 average rating, 42 reviews

Guest favourite

Home in Shelter Island

Hamptons - Shelter Island Farmhouse

4 bedrooms, 4 beds, 2 bathrooms

5–10 Oct

$5,566 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

$5,200 SGD for 5 nights

4.93 out of 5 average rating, 44 reviews