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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

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4.9 out of 5 average rating, 126 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

$1,524 SGD for 5 nights

4.91 out of 5 average rating, 136 reviews

Home in Shelter Island

Hamptons area Estate on Water w Boat Dock & pool.

6 bedrooms, 8 beds, 7 bathrooms

1–8 Jul

$23,542 SGD for 7 nights

Guest favourite

Room in Shelter Island

Magnolia Cape with private entrance & private bath

1 king bed, 1 bathroom

5–10 Jul

$1,753 SGD for 5 nights

4.83 out of 5 average rating, 41 reviews

Guest favourite

Room in Shelter Island

A room in a sunny cottage with use of pool.

1 king bed, 1 bathroom

11–16 Aug

$1,913 SGD for 5 nights

4.95 out of 5 average rating, 146 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

1–6 Aug

$5,981 SGD for 5 nights

Pay $0 today

Free cancellation

4.92 out of 5 average rating, 12 reviews

Top guest favourite

Room in Shelter Island

Master Suite at RedHouse

1 king bed, 1 bathroom

5–10 Jul

$1,623 SGD for 5 nights

4.95 out of 5 average rating, 165 reviews

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

23–28 Jul

$7,086 SGD for 5 nights

4.91 out of 5 average rating, 91 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

$12,800 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$10,362 SGD for 5 nights

Pay $0 today

Free cancellation

4.94 out of 5 average rating, 35 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, 27 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

New place to stay

Guest favourite

Room in Shelter Island

Candlelite Inn Queen Onsuite Bath

1 queen bed, 1 bathroom

4–9 Jul

$2,553 SGD for 5 nights

4.91 out of 5 average rating, 45 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

Top guest favourite

Rooms in Shelter Island

Grace House

2 bedrooms, 2 beds, 1 bathroom

13–18 Sept

$2,400 SGD for 5 nights

5.0 out of 5 average rating, 48 reviews

Top guest favourite

Guest house in Shelter Island

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds, 1 bathroom

12–17 Sept

$3,086 SGD for 5 nights

Pay $0 today

Free cancellation

4.99 out of 5 average rating, 73 reviews

Guest favourite

Cottage in Shelter Island

Charming Coastal Cottage

3 bedrooms, 3 beds, 1.5 bathrooms

5–10 Jul

$5,867 SGD for 5 nights

Pay $0 today

Free cancellation

4.84 out of 5 average rating, 44 reviews

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds, 1 bathroom

13–18 Sept

$3,536 SGD for 5 nights

4.84 out of 5 average rating, 74 reviews

Guest favourite

Rooms in Shelter Island

Room in Charming Coastal Cottage

2 bedrooms, 1 bed, 2 bathrooms

19–24 Jul

$1,197 SGD for 5 nights

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 25 reviews