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Search results; Over 1,000 homes in Shelter Island

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Guest favourite
Home in Shelter Island
Hay Beach Family Home: Fire Pit, Playroom, Yard
3 bedrooms, 4 beds, 2 private bathrooms
6–11 Sept
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4.9 out of 5 average rating, 129 reviews
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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
4.92 out of 5 average rating, 154 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Sept
New place to stay
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Guest favourite
Home in Shelter Island
Private Shelter Island Escape | Huge Yard + Pool
4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 43 reviews
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Top guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 172 reviews
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Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
1–6 Sept
4.95 out of 5 average rating, 170 reviews
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Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 129 reviews
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Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.97 out of 5 average rating, 79 reviews
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Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Shelter Island
Shelter Island Beauty w/Pool; Beaches/Golf/Tennis
4 bedrooms, 5 beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 16 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, 2 bathrooms
20–27 Sept
5.0 out of 5 average rating, 77 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 bathroom
1–6 Oct
4.95 out of 5 average rating, 151 reviews
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Home in Shelter Island
Shelter Island's Silver Beach Home
3 bedrooms, 6 beds, 2.5 bathrooms
2–7 Sept
4.92 out of 5 average rating, 26 reviews
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Guest favourite
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 bathrooms
9–16 Sept
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
1 king bed, 1 bathroom
13–18 Sept
4.86 out of 5 average rating, 49 reviews
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Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Sept
4.93 out of 5 average rating, 14 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
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
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Guest favourite
Home in Shelter Island Heights
Gingerbread Cottage
5 bedrooms, 6 beds, 4.5 bathrooms
9–16 Sept
5.0 out of 5 average rating, 11 reviews