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Search results; Over 1,000 homes in Shelter Island Heights

Loft in Shelter Island Heights

Waterfront jewel box on a high bluff.

1 bedroom, 2 beds, 1 shared bathroom

8–15 Sept

$7,861 SGD for 7 nights

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Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

5–11 Aug

$7,803 SGD for 6 nights

Pay $0 today

Free cancellation

Guest favourite

Home in Shelter Island

Charming Farmhouse with Pool

6 bedrooms, 3 bathrooms

1–6 Aug

$5,977 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

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$10,020 SGD for 5 nights

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Free cancellation

4.95 out of 5 average rating, 40 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds, 2 bathrooms

10–15 Aug

$6,484 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, 2.5 bathrooms

2–7 Aug

$5,433 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

$5,974 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

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

14–19 Aug

$7,340 SGD for 5 nights

4.91 out of 5 average rating, 94 reviews

Home in Sag Harbor

Shelter Island Shell Beach Oasis

4 bedrooms, 5 beds, 3 bathrooms

3–8 Aug

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Free cancellation

New place to stay

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

1–6 Aug

$12,937 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Home in Shelter Island

Private Shelter Island Escape | Huge Yard + Pool

4 bedrooms, 5 beds, 2.5 bathrooms

9–14 Aug

$10,128 SGD for 5 nights

Top guest favourite

Home in Greenport

Greenport Gem

2 bedrooms, 2 beds, 1 bathroom

2–7 Aug

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 26 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

Guest favourite

Home in Shelter Island

Peaceful Bright Country House

3 bedrooms, 3 beds, 2 bathrooms

8–13 Sept

$4,559 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Guest house in Shelter Island

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds, 1 bathroom

1–6 Aug

$3,158 SGD for 5 nights

Pay $0 today

Free cancellation

4.99 out of 5 average rating, 74 reviews

Top guest favourite

Home in Greenport

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

3 bedrooms, 3 beds, 2 bathrooms

9–14 Aug

$4,995 SGD for 5 nights

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 54 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

Guest favourite

Home in Shelter Island

Mid-Century Gem with Pool. Steps to Private Beach.

3 bedrooms, 3 beds, 2.5 bathrooms

7–14 Sept

$13,205 SGD for 7 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Cottage in Shelter Island

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds, 2 bathrooms

10–15 Aug

$7,005 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews