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

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Loft in Shelter Island Heights
Waterfront jewel box on a high bluff.
1 bedroom, 2 beds, 1 shared bathroom
2–9 Oct
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Featured hotel
Hotel in Greenport
Oyster Estate, Classic king
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
New place to stay
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Top guest favourite
Room in Shelter Island
Casual Island Getaway - Walk to the Beach
1 queen bed, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 162 reviews
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Guest favourite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
4 bedrooms, 4 beds, 3 bathrooms
2–7 Oct
5.0 out of 5 average rating, 22 reviews
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Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 131 reviews
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Top guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 80 reviews
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 45 reviews
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Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 32 reviews
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Flat in Shelter Island Heights
5 star Waterfront cottage at Dering Harbor Inn.
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
New place to stay
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Home in Shelter Island Heights
Spacious beach house with stunning water views.
5 bedrooms, 8 beds, 4 bathrooms
4–11 Oct
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
1–6 Oct
4.82 out of 5 average rating, 84 reviews
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Guest favourite
Home in Shelter Island
Moonlit Manor | Shelter Island Escape w/ Sauna
3 bedrooms, 3 beds, 2 bathrooms
3–10 Oct
4.94 out of 5 average rating, 18 reviews
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Guest favourite
Room in Shelter Island
Candlelite Inn Queen Onsuite Bath
1 queen bed, 1 bathroom
1–6 Oct
4.92 out of 5 average rating, 51 reviews
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Guest favourite
Home in Shelter Island
Chic, serene, designer home with pool and views
4 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.98 out of 5 average rating, 44 reviews
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Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds, 2 bathrooms
22–27 May
5.0 out of 5 average rating, 27 reviews
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Home in Shelter Island
Shelter Island House with water views & cottage
5 bedrooms, 6 beds, 3 bathrooms
2–7 Oct
4.8 out of 5 average rating, 5 reviews
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Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Shelter Island
Newly Renovated w/ Pool, Hot tub & Fireplace
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.92 out of 5 average rating, 36 reviews
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Top guest favourite
Home in Shelter Island
Family Friendly Oasis Steps to Water - Heated Pool
6 bedrooms, 9 beds, 3 bathrooms
1–6 Dec
5.0 out of 5 average rating, 46 reviews