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Search results; Over 1,000 homes in Shelter Island

Room in Shelter Island
Queen room with ensuite bathroom
Studio, 1 bed, 1 private bath
Aug 18 – 23
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Top guest favorite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 bedroom, 1 queen bed, 1 bath
Oct 4 – 9
4.92 out of 5 average rating, 149 reviews
Top guest favorite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 baths
Sep 6 – 11
4.97 out of 5 average rating, 127 reviews
Top guest favorite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 baths
Sep 6 – 11
4.95 out of 5 average rating, 41 reviews
Top guest favorite
Guesthouse in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bath
Sep 7 – 12
4.99 out of 5 average rating, 77 reviews
Guest favorite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 8 reviews
Top guest favorite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bath
Aug 23 – 28
4.95 out of 5 average rating, 168 reviews
Guest favorite
Cottage in Shelter Island
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
4.93 out of 5 average rating, 27 reviews
Top guest favorite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 baths
Aug 14 – 19
4.93 out of 5 average rating, 86 reviews
Guest favorite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
1 king bed, 1 bath
Aug 16 – 21
4.85 out of 5 average rating, 46 reviews
Top guest favorite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds, 2 baths
Sep 20 – 27
5.0 out of 5 average rating, 76 reviews
Guest favorite
Room in Shelter Island
A room in a sunny cottage with use of pool.
1 king bed, 1 bath
Oct 1 – 6
4.95 out of 5 average rating, 149 reviews
Top guest favorite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4
4.98 out of 5 average rating, 54 reviews
Top guest favorite
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 baths
Sep 9 – 16
5.0 out of 5 average rating, 13 reviews
Guest favorite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds, 3.5 baths
Oct 4 – 9
4.95 out of 5 average rating, 76 reviews
Guest favorite
Guesthouse in Shelter Island
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds, 1 bath
Aug 24 – 29
5.0 out of 5 average rating, 6 reviews
Top guest favorite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds, 2.5 baths
Sep 20 – 25
4.93 out of 5 average rating, 44 reviews
Guest favorite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds, 2 baths
Apr 17 – 22
5.0 out of 5 average rating, 24 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 baths
Aug 13 – 20
5.0 out of 5 average rating, 3 reviews