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Search results; Over 1,000 homes in Shelter Island

Home in Shelter Island

Waterfront Haven

5 bedrooms, 9 beds, 4.5 private bathrooms

8–13 Sept

$6,320 SGD for 5 nights

,

4.88 out of 5 average rating, 17 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds

9–14 Aug

$10,355 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 37 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds

13–18 Jul

$6,853 SGD for 5 nights

4.93 out of 5 average rating, 84 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds

12–17 Jul

$4,439 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

23–30 Aug

$6,032 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

8–13 Jul

$13,248 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Place to stay in Shelter Island

Casual Island Getaway - Walk to the Beach

1 bedroom, 1 queen bed

4–9 Oct

$1,219 SGD for 5 nights

4.91 out of 5 average rating, 138 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds

13–20 Jul

$7,009 SGD for 7 nights

Free cancellation

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds

23–28 Jul

$7,081 SGD for 5 nights

4.91 out of 5 average rating, 93 reviews

Top guest favourite

Cottage in Shelter Island

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds

30 Aug – 4 Sept

$7,009 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds

13–18 Sept

$3,533 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

3–8 Aug

$5,977 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds

4–9 Oct

$6,244 SGD for 5 nights

4.94 out of 5 average rating, 72 reviews

Top guest favourite

Home in Shelter Island

CASA GYPSEA - a chic and peaceful 3 bedroom house

3 bedrooms, 3 beds

20–27 Sept

5.0 out of 5 average rating, 73 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Oasis Steps to Water - Heated Pool

6 bedrooms, 9 beds

23–28 Aug

$11,994 SGD for 5 nights

5.0 out of 5 average rating, 40 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

Guest favourite

Home in Shelter Island

Hamptons - Shelter Island Farmhouse

4 bedrooms, 4 beds

5–10 Oct

$5,558 SGD for 5 nights

4.94 out of 5 average rating, 51 reviews

Guest favourite

Rooms in Shelter Island

Grace House

2 bedrooms, 2 beds

13–18 Sept

$2,399 SGD for 5 nights

5.0 out of 5 average rating, 48 reviews

Guest favourite

Cottage in Shelter Island

Charming Coastal Cottage

3 bedrooms, 3 beds

12–17 Jul

$6,472 SGD for 5 nights

4.84 out of 5 average rating, 44 reviews