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Search results; Over 1,000 homes in Shelter Island

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Holiday home in Shelter Island
The Perfect Shelter Island Getaway! With Pool
3 bedrooms, 6 beds, 2.5 private bathrooms
11–16 Oct
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5.0 out of 5 average rating, 4 reviews
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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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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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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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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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Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 77 reviews
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Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.93 out of 5 average rating, 45 reviews
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Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
4 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 22 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
New place to stay
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Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds, 1 bathroom
12–17 Oct
4.97 out of 5 average rating, 172 reviews
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Home in Shelter Island
Shelter Island 4 BR w Pool & Private Beach Access
4 bedrooms, 7 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 12 reviews
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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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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
Peaceful Bright Country House
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 11 reviews
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Home in Shelter Island
Private Hay Beach Retreat with Heated Pool
4 bedrooms, 5 beds, 3 bathrooms
25–30 Oct
4.98 out of 5 average rating, 94 reviews
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Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 bathrooms
1–8 Oct
5.0 out of 5 average rating, 14 reviews
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Room in Shelter Island
A room in a sunny cottage with use of pool.
1 king bed, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 155 reviews
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Home in Shelter Island
Shelter Island Retreat | 3 King Beds + Huge Yard
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 6 reviews
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Home in Sag Harbor
Sag Harbor Getaway | Private Beach | Hamptons
4 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
New place to stay