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Search results; Over 1,000 homes in Shelter Island

Top guest favorite
Home in Shelter Island Heights
Mid-century modern with a heated pool
3 bedrooms, 5 beds, 2 private baths
Sep 8 – 13
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4.91 out of 5 average rating, 35 reviews
Top guest favorite
Cottage in Shelter Island
Heated saltwater pool on 5 acres
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 6 beds, 1.5 baths
Sep 6 – 11
Top guest favorite
Place to stay in Shelter Island
Shelter Island retreat with private entrance
4.92 out of 5 average rating, 149 reviews, 1 bedroom, 1 bed, 1 bath
Oct 4 – 9
Top guest favorite
Cottage in Shelter Island
Shelter Island village with bikes and kayak
4.97 out of 5 average rating, 127 reviews, 3 bedrooms, 4 beds, 2.5 baths
Sep 6 – 11
Top guest favorite
Guesthouse in Shelter Island Heights
Bayfront with a pool and private dock
4.99 out of 5 average rating, 77 reviews, 1 bedroom, 2 beds, 1 bath
Sep 7 – 12
Guest favorite
Home in Shelter Island Heights
Water views on 3 sides with pool
4.95 out of 5 average rating, 76 reviews, 5 bedrooms, 9 beds, 3.5 baths
Oct 4 – 9
Top guest favorite
Room in Shelter Island Heights
1800s farmhouse with a fire pit
4.95 out of 5 average rating, 168 reviews, 1 king bed, 1 bath
Aug 23 – 28
Top guest favorite
Home in Shelter Island Heights
Cedar-shingled ranch with pool near beach
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 6 beds, 2 baths
Sep 9 – 16
Top guest favorite
Home in Shelter Island Heights
Heated saltwater pool on Shelter Island
5.0 out of 5 average rating, 76 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 20 – 27
Top guest favorite
Guest suite in Shelter Island Heights
Renovated suite minutes from the beach
4.98 out of 5 average rating, 54 reviews, 1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4
Guest favorite
Cottage in Shelter Island Heights
Waterfront views from every room
4.93 out of 5 average rating, 27 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
Top guest favorite
Home in Shelter Island Heights
Huge yard with beach a bike away
4.93 out of 5 average rating, 86 reviews, 4 bedrooms, 5 beds, 2 baths
Aug 14 – 19
Guest favorite
Home in Shelter Island
New build with pool and beach access
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 baths
Aug 30 – Sep 4
Guest favorite
Cottage in Shelter Island Heights
Bayfront cottage on a historic estate
4.85 out of 5 average rating, 78 reviews, 3 bedrooms, 4 beds, 1 bath
Sep 13 – 18
Top guest favorite
Home in Shelter Island
Renovated mid-century home near the beach
4.93 out of 5 average rating, 44 reviews, 3 bedrooms, 4 beds, 2.5 baths
Sep 20 – 25
Home in Shelter Island
Quiet street, walking distance to beach
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1.5 baths
Aug 30 – Sep 4
Top guest favorite
Home in Shelter Island Heights
Mid-century ranch with pool and Jacuzzi
4.92 out of 5 average rating, 96 reviews, 4 bedrooms, 4 beds, 2 baths
Nov 1 – 6
Guest favorite
Cottage in Shelter Island
Walk to the beach from a quiet road
4.85 out of 5 average rating, 47 reviews, 3 bedrooms, 3 beds, 1.5 baths
Oct 1 – 6
Guest favorite
Home in Shelter Island
Cape Cod on one acre with fire pit
5.0 out of 5 average rating, 24 reviews, 5 bedrooms, 5 beds, 2 baths
Apr 17 – 22