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Search results; Over 1,000 homes in Shelter Island

Guest favourite

Home in Shelter Island

Peaceful Bright Country House

3 bedrooms, 3 beds, 2 private bathrooms

8–13 Sept

$4,556 SGD for 5 nights

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5.0 out of 5 average rating, 9 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

9–14 Aug

$10,069 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 40 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

$1,185 SGD for 5 nights

4.92 out of 5 average rating, 142 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

17–22 Jul

$12,014 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

2–7 Aug

$5,429 SGD for 5 nights

4.97 out of 5 average rating, 122 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

3–8 Aug

$5,969 SGD for 5 nights

Pay $0 today

Free cancellation

4.92 out of 5 average rating, 13 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds, 2 bathrooms

10–15 Aug

$6,479 SGD for 5 nights

4.93 out of 5 average rating, 84 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds, 2 bathrooms

23–30 Aug

$6,028 SGD for 7 nights

5.0 out of 5 average rating, 24 reviews

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds, 1 bathroom

13–18 Sept

$3,529 SGD for 5 nights

4.84 out of 5 average rating, 76 reviews

Home in Shelter Island

Private Shelter Island Escape | Huge Yard + Pool

4 bedrooms, 5 beds, 2.5 bathrooms

9–14 Aug

$10,120 SGD for 5 nights

Top guest favourite

Room in Shelter Island

Master Suite at RedHouse

1 king bed, 1 bathroom

19–24 Jul

$1,483 SGD for 5 nights

4.95 out of 5 average rating, 166 reviews

Guest favourite

Home in Shelter Island

Charming Farmhouse with Pool

6 bedrooms, 3 bathrooms

31 Jul – 5 Aug

$6,540 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Cottage in Shelter Island

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds, 2 bathrooms

10–15 Aug

$6,999 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

$6,236 SGD for 5 nights

4.95 out of 5 average rating, 74 reviews

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

14–19 Aug

$7,528 SGD for 5 nights

4.91 out of 5 average rating, 94 reviews

Guest favourite

Rooms in Shelter Island

Grace House

2 bedrooms, 2 beds, 1 bathroom

13–18 Sept

$2,396 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, 2 bathrooms

20–27 Sept

5.0 out of 5 average rating, 74 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

17–22 Jul

$5,152 SGD for 5 nights

Pay $0 today

Free cancellation

Top guest favourite

Home in Shelter Island

Private Hay Beach Retreat with Heated Pool

4 bedrooms, 5 beds, 3 bathrooms

3–10 Aug

4.98 out of 5 average rating, 93 reviews