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Search results; Over 1,000 homes in Shelter Island

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Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 private bathrooms
26 Sept – 1 Oct
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4.97 out of 5 average rating, 131 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
20–25 Sept
4.95 out of 5 average rating, 44 reviews
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Guest favourite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
4 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds
20–25 Sept
4.93 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds
18–25 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 77 reviews
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Top guest favourite
Home in Shelter Island
Shelter Island 4 BR w Pool & Private Beach Access
4 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds
20–25 Sept
4.97 out of 5 average rating, 172 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds
21–26 Sept
New place to stay
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Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds
5–10 Oct
4.93 out of 5 average rating, 88 reviews
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Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds
18–23 Sept
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds
30 Sept – 5 Oct
4.82 out of 5 average rating, 84 reviews
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Top guest favourite
Home in Shelter Island
Private Hay Beach Retreat with Heated Pool
4 bedrooms, 5 beds
25–30 Oct
4.98 out of 5 average rating, 94 reviews
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Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds
30 Sept – 7 Oct
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Flat in Shelter Island Heights
5 star Waterfront cottage at Dering Harbor Inn.
1 bedroom, 3 beds
20–25 Sept
New place to stay
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Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds
1–6 Nov
4.92 out of 5 average rating, 100 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, 154 reviews