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Search results; Over 1,000 homes in Shelter Island

Guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds, 3.5 private bathrooms
4–9 Oct
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4.95 out of 5 average rating, 74 reviews
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
4.91 out of 5 average rating, 141 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
4.83 out of 5 average rating, 42 reviews, 1 king bed, 1 bathroom
19–24 Jul
Guest favourite
Room in Shelter Island
A room in a sunny cottage with use of pool.
4.95 out of 5 average rating, 146 reviews, 1 king bed, 1 bathroom
29 Sept – 4 Oct
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
13–20 Jul
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
13–18 Jul
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
4.95 out of 5 average rating, 165 reviews, 1 king bed, 1 bathroom
15–20 Jul
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 39 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
4.97 out of 5 average rating, 120 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4.91 out of 5 average rating, 93 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
Home in Shelter Island
Captain Don’s Paradise
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
Top guest favourite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
4.98 out of 5 average rating, 52 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
5.0 out of 5 average rating, 29 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
27 Aug – 1 Sept
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4.93 out of 5 average rating, 84 reviews, 4 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 1 bed, 2 bathrooms
19–24 Jul
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
4.84 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
Guest favourite
Cottage in Shelter Island
Charming Coastal Cottage
4.85 out of 5 average rating, 46 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug
Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
5.0 out of 5 average rating, 74 reviews, 3 bedrooms, 3 beds, 2 bathrooms
20–27 Sept
Guest favourite
Room in Shelter Island
Candlelite Inn Queen Onsuite Bath
4.91 out of 5 average rating, 46 reviews, 1 queen bed, 1 bathroom
19–24 Jul