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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
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.91 out of 5 average rating, 139 reviews
Guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
1 king bed, 1 bathroom
16–21 Jul
4.83 out of 5 average rating, 42 reviews
Guest favourite
Room in Shelter Island
A room in a sunny cottage with use of pool.
1 king bed, 1 bathroom
29 Sept – 4 Oct
4.95 out of 5 average rating, 146 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.97 out of 5 average rating, 118 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
10–15 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
4.95 out of 5 average rating, 38 reviews
Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
4 bedrooms, 5 beds, 2.5 bathrooms
10–15 Jul
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
15–20 Jul
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
1 bedroom, 1 bed, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 50 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
13–20 Jul
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, 74 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
4.91 out of 5 average rating, 93 reviews
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
2 bedrooms, 1 bed, 2 bathrooms
19–24 Jul
4.96 out of 5 average rating, 26 reviews
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
17–22 Aug
4.84 out of 5 average rating, 75 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
13–18 Jul
4.93 out of 5 average rating, 84 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
8–15 Aug
4.99 out of 5 average rating, 74 reviews
Guest favourite
Room in Shelter Island
Candlelite Inn Queen Onsuite Bath
1 queen bed, 1 bathroom
19–24 Jul
4.91 out of 5 average rating, 46 reviews