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Search results; Over 1,000 homes in Shelter Island

Top guest favourite

Guest house in Shelter Island

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds, 1 private bathroom

9–14 Aug

$3,121 SGD for 5 nights

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4.99 out of 5 average rating, 74 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

$1,186 SGD for 5 nights

4.92 out of 5 average rating, 142 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

30 Aug – 4 Sept

$4,990 SGD for 5 nights

4.97 out of 5 average rating, 122 reviews

Guest favourite

Room in Shelter Island

Magnolia Cape with private entrance & private bath

1 king bed, 1 bathroom

9–14 Aug

$1,704 SGD for 5 nights

4.84 out of 5 average rating, 44 reviews

Top guest favourite

Guest suite in Shelter Island

Chic and Cozy Suite with Private Entrance

1 bedroom, 1 bed, 1 bathroom

2–7 Aug

$2,069 SGD for 5 nights

4.98 out of 5 average rating, 52 reviews

Guest favourite

Room in Shelter Island

A room in a sunny cottage with use of pool.

1 king bed, 1 bathroom

1–6 Oct

$1,911 SGD for 5 nights

4.95 out of 5 average rating, 147 reviews

Guest favourite

Rooms in Shelter Island

Room in Charming Coastal Cottage

2 bedrooms, 1 bed, 2 bathrooms

13–18 Sept

$1,195 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 26 reviews

Top guest favourite

Room in Shelter Island

Master Suite at RedHouse

1 king bed, 1 bathroom

21–26 Aug

$1,637 SGD for 5 nights

4.95 out of 5 average rating, 166 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

$5,192 SGD for 7 nights

5.0 out of 5 average rating, 75 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$10,020 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 40 reviews

Home in Shelter Island

Private Shelter Island Escape | Huge Yard + Pool

4 bedrooms, 5 beds, 2.5 bathrooms

9–14 Aug

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Shelter Island

Light, spacious 3bdr home steps to Wades Beach

3 bedrooms, 4 beds, 2.5 bathrooms

2–7 Sept

$6,355 SGD for 5 nights

4.93 out of 5 average rating, 44 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds, 2 bathrooms

23–30 Aug

$6,037 SGD for 7 nights

5.0 out of 5 average rating, 24 reviews

Guest favourite

Home in Shelter Island

Stunning water views, huge pool, family resort

4 bedrooms, 6 beds, 3 bathrooms

2–7 Sept

$11,111 SGD for 5 nights

4.93 out of 5 average rating, 57 reviews

Guest house in Shelter Island

Modern Waterfront Cottage Oasis

1 bedroom, 2 beds, 1 bathroom

1–6 Aug

$7,230 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Guest favourite

Room in Shelter Island

Candlelite Inn Queen Onsuite Bath

1 queen bed, 1 bathroom

11–16 Aug

$2,550 SGD for 5 nights

4.91 out of 5 average rating, 46 reviews

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds, 1 bathroom

13–18 Sept

$3,532 SGD for 5 nights

4.84 out of 5 average rating, 76 reviews

Home in Shelter Island

Private Island retreat, beach and nature nearby !

3 bedrooms, 4 beds, 2 bathrooms

2–7 Aug

$5,518 SGD for 5 nights

Free cancellation

Apartment in Greenport

Water front, sunsets, sail boats, 30 day minimum

2 bedrooms, 2 beds, 2 bathrooms

1–6 Aug

$4,300 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews