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Search results; Over 1,000 homes in Shelter Island

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$9,925 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 41 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

6–11 Sept

$4,282 SGD for 5 nights

4.97 out of 5 average rating, 125 reviews

Top guest favourite

Guest house in Shelter Island Heights

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds, 1 bathroom

7–12 Sept

$3,053 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 76 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

$1,139 SGD for 5 nights

4.92 out of 5 average rating, 144 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

30 Aug – 4 Sept

$12,588 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds, 2 bathrooms

17–22 Apr

$5,088 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

Top guest favourite

Home in Shelter Island Heights

Family Friendly Island Home

4 bedrooms, 5 beds, 2 bathrooms

10–15 Aug

$6,423 SGD for 5 nights

4.93 out of 5 average rating, 85 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

$5,009 SGD for 5 nights

4.93 out of 5 average rating, 44 reviews

Guest favourite

Cottage in Shelter Island Heights

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds, 2 bathrooms

10–15 Aug

$6,939 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews

Guest favourite

Cottage in Shelter Island Heights

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds, 1 bathroom

13–18 Sept

$3,498 SGD for 5 nights

4.84 out of 5 average rating, 77 reviews

Top guest favourite

Home in Shelter Island Heights

Shelter Island Home with Large Yard And Pool

3 bedrooms, 6 beds, 2 bathrooms

9–16 Sept

$6,572 SGD for 7 nights

5.0 out of 5 average rating, 13 reviews

Guest favourite

Home in Shelter Island Heights

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$6,022 SGD for 5 nights

4.95 out of 5 average rating, 76 reviews

Guest favourite

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

9–14 Aug

$5,918 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Top guest favourite

Home in Shelter Island Heights

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, 76 reviews

Top guest favourite

Home in Shelter Island Heights

Private Hay Beach Retreat with Heated Pool

4 bedrooms, 5 beds, 3 bathrooms

5–10 Oct

$6,432 SGD for 5 nights

4.98 out of 5 average rating, 93 reviews

Top guest favourite

Home in Shelter Island Heights

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

1–6 Nov

$3,230 SGD for 5 nights

4.92 out of 5 average rating, 95 reviews

Top guest favourite

Room in Shelter Island Heights

Master Suite at RedHouse

1 king bed, 1 bathroom

21–26 Aug

$1,621 SGD for 5 nights

4.95 out of 5 average rating, 168 reviews

Guest favourite

Room in Shelter Island

Magnolia Cape with private entrance & private bath

1 king bed, 1 bathroom

9–14 Aug

$1,687 SGD for 5 nights

4.85 out of 5 average rating, 46 reviews