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Search results; Over 1,000 homes in Shelter Island

Home in Shelter Island

Waterfront Estate on Shelter Island. 100 Ft Dock

4 bedrooms, 4 beds, 3 private bathrooms

3–9 Aug

$8,203 SGD for 6 nights

,

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Rooms in Shelter Island

Grace House

2 bedrooms, 2 beds

5–10 Jul

$2,183 SGD for 5 nights

5.0 out of 5 average rating, 48 reviews

Guest favourite

Room in Shelter Island

Candlelite Inn Queen Onsuite Bath

1 queen bed

5–10 Jul

$2,408 SGD for 5 nights

4.91 out of 5 average rating, 45 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds

5–10 Jul

$12,841 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

1–6 Sept

$1,529 SGD for 5 nights

4.91 out of 5 average rating, 134 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds

6–11 Sept

$10,395 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 35 reviews

Top guest favourite

Home in Shelter Island Heights

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds

23–28 Jul

$7,109 SGD for 5 nights

4.91 out of 5 average rating, 90 reviews

Guest favourite

Room in Shelter Island

Magnolia Cape with private entrance & private bath

1 king bed

5–10 Jul

$1,758 SGD for 5 nights

4.82 out of 5 average rating, 39 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds

1–6 Aug

$6,000 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 12 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds

12–17 Jul

$5,603 SGD for 5 nights

4.97 out of 5 average rating, 116 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds

25–30 Jul

$4,705 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

Top guest favourite

Cottage in Shelter Island Heights

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds

30 Aug – 4 Sept

$7,036 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews

Top guest favourite

Room in Shelter Island Heights

Master Suite at RedHouse

1 king bed

5–10 Jul

$1,629 SGD for 5 nights

4.95 out of 5 average rating, 164 reviews

Guest favourite

Room in Shelter Island

A room in a sunny cottage with use of pool.

1 king bed

27 Jul – 1 Aug

$1,904 SGD for 5 nights

4.95 out of 5 average rating, 146 reviews

Guest favourite

Home in Shelter Island

Shelter Island 4 bed waterfront home with office

4 bedrooms, 5 beds

5–10 Jul

5.0 out of 5 average rating, 27 reviews

Guest favourite

Cottage in Shelter Island Heights

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds

13–18 Sept

$3,547 SGD for 5 nights

4.84 out of 5 average rating, 73 reviews

Top guest favourite

Home in Shelter Island Heights

Family Friendly Island Home

4 bedrooms, 5 beds

13–18 Jul

$6,879 SGD for 5 nights

4.93 out of 5 average rating, 83 reviews

Guest favourite

Home in Shelter Island Heights

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds

4–9 Oct

$6,268 SGD for 5 nights

4.94 out of 5 average rating, 72 reviews

Top guest favourite

Home in Shelter Island Heights

CASA GYPSEA - a chic and peaceful 3 bedroom house

3 bedrooms, 3 beds

25 Jul – 1 Aug

$9,631 SGD for 7 nights

5.0 out of 5 average rating, 71 reviews