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Search results; Over 1,000 homes in Shelter Island

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Top guest favourite
Home in Shelter Island
Newly Renovated w/ Pool, Hot tub & Fireplace
3 bedrooms, 5 beds, 2 private bathrooms
1–6 Oct
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4.92 out of 5 average rating, 36 reviews
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Top guest favourite
Room in Shelter Island
Casual Island Getaway - Walk to the Beach
1 queen bed
4–9 Oct
4.93 out of 5 average rating, 162 reviews
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Top guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds
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
1–6 Oct
4.96 out of 5 average rating, 45 reviews
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Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds
1–6 Oct
4.97 out of 5 average rating, 131 reviews
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Top guest favourite
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds
1–8 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds
1–6 Oct
4.93 out of 5 average rating, 45 reviews
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Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds
22–27 May
5.0 out of 5 average rating, 27 reviews
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Guest favourite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
4 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 21 reviews
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Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds
1–6 Oct
4.82 out of 5 average rating, 84 reviews
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Guest favourite
Home in Shelter Island Heights
Gingerbread Cottage
5 bedrooms, 6 beds
2–9 Oct
5.0 out of 5 average rating, 11 reviews
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Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds
1–8 Oct
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds
1–6 Oct
New place to stay
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Guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds
12–17 Oct
4.97 out of 5 average rating, 172 reviews
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Guest favourite
Room in Shelter Island
A room in a sunny cottage with use of pool.
1 king bed
1–6 Oct
4.95 out of 5 average rating, 155 reviews
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Featured hotel
Hotel in Greenport
Oyster Estate, Classic king
1 bedroom, 1 king bed
4–9 Oct
New place to stay
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Home in Shelter Island
Waterfront Remodeled Cape Cod House & Dock
5 bedrooms, 6 beds
18–23 Jun
New place to stay
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Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 77 reviews
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Guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed
4–9 Oct
4.94 out of 5 average rating, 174 reviews