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Search results; Over 1,000 homes in Shelter Island

Top guest favorite
This bayfront Shelter Island guesthouse gives you a saltwater pool and private dock
1 bedroom, 2 beds, 1 private bath
Sep 7 – 12
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4.99 out of 5 average rating, 77 reviews
Top guest favorite
This Shelter Island cottage gives you 5 acres, a heated saltwater pool, and a pond
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 6 beds, 1.5 baths
Sep 6 – 11
Top guest favorite
Private room
This Shelter Island room gives you a private entrance and wooded deck near the beach
4.92 out of 5 average rating, 149 reviews, 1 bedroom, 1 bed, 1 bath
Oct 4 – 9
Top guest favorite
This Shelter Island cottage puts you across from tennis courts, with bikes and a kayak
4.97 out of 5 average rating, 127 reviews, 3 bedrooms, 4 beds, 2.5 baths
Sep 6 – 11
Guest favorite
Water views on three sides greet you at this Suffolk County house with a pool
4.95 out of 5 average rating, 76 reviews, 5 bedrooms, 9 beds, 3.5 baths
Oct 4 – 9
Top guest favorite
Private room
A renovated 1800s farmhouse suite on Shelter Island where you’ll have a fire pit and hammocks
4.95 out of 5 average rating, 168 reviews, 1 king bed, 1 bath
Aug 23 – 28
Top guest favorite
This cedar-shingled Shelter Island ranch gives you a pool, large deck, and yard
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 6 beds, 2 baths
Sep 9 – 16
Top guest favorite
This Shelter Island house gives you a heated saltwater pool and lush private gardens
5.0 out of 5 average rating, 76 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 20 – 27
Top guest favorite
Private room
This serene Long Island suite gives you a private entrance and beach towels
4.98 out of 5 average rating, 54 reviews, 1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4
Guest favorite
Waterfront views from every room greet you at this Shelter Island cottage
4.93 out of 5 average rating, 27 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
Top guest favorite
A Shelter Island house with a huge sunny yard, fireplace, and outdoor shower
4.93 out of 5 average rating, 86 reviews, 4 bedrooms, 5 beds, 2 baths
Aug 14 – 19
Guest favorite
This newly built Long Island house gives you a private pool and alfresco dining
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 baths
Aug 30 – Sep 4
Guest favorite
Wake to bay and pond views at this cottage on a historic Shelter Island estate
4.85 out of 5 average rating, 78 reviews, 3 bedrooms, 4 beds, 1 bath
Sep 13 – 18
Top guest favorite
This mid-century Shelter Island home puts you three houses from the beach
4.93 out of 5 average rating, 44 reviews, 3 bedrooms, 4 beds, 2.5 baths
Sep 20 – 25
This Long Island house puts you on a quiet street near the beach
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1.5 baths
Aug 30 – Sep 4
Top guest favorite
This mid-century Shelter Island ranch gives you a pool, jacuzzi, and giant deck
4.92 out of 5 average rating, 96 reviews, 4 bedrooms, 4 beds, 2 baths
Nov 1 – 6
Guest favorite
This bright Suffolk County cottage gives you a private deck, grill, and large yard
4.85 out of 5 average rating, 47 reviews, 3 bedrooms, 3 beds, 1.5 baths
Oct 1 – 6
Guest favorite
This Shelter Island Cape Cod gives you a fire pit, huge deck, and wooded acre
5.0 out of 5 average rating, 24 reviews, 5 bedrooms, 5 beds, 2 baths
Apr 17 – 22
Guest favorite
This newly built Shelter Island cottage puts you right on the water with dock access
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bath
Aug 24 – 29