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Search results; Over 1,000 homes in Shelter Island Heights

Guest favorite
Room in Shelter Island Heights
Resort-style inn one block from beach
1 bedroom, 1 bed, 1 shared bath
Aug 23 – 28
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5.0 out of 5 average rating, 5 reviews
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
Place to stay in Shelter Island
Shelter Island retreat with private entrance
4.92 out of 5 average rating, 148 reviews, 1 bedroom, 1 bed, 1 bath
Oct 4 – 9
Guest favorite
Rooms in Shelter Island Heights
Award-winning inn near Crescent Beach
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 1 king bed, 1 bath
Aug 16 – 21
Home in Shelter Island Heights
Century-old shingle house on the creek
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 3.5 baths
Aug 12 – 19
Top guest favorite
Guesthouse in Shelter Island
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
Room in Shelter Island
Soaking tub and a private backyard
4.85 out of 5 average rating, 46 reviews, 1 king bed, 1 bath
Aug 16 – 21
Top guest favorite
Guest suite in Shelter Island
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
Top guest favorite
Rooms in Greenport
Restored 1859 Italianate near the beach
5.0 out of 5 average rating, 98 reviews, 2 bedrooms, 3 queen beds, No bathroom
Sep 6 – 11
Guest favorite
Guesthouse in Shelter Island
Newly built waterfront with dock and kayaks
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bath
Aug 24 – 29
Top guest favorite
Room in Shelter Island
1800s farmhouse with a fire pit
4.95 out of 5 average rating, 168 reviews, 1 king bed, 1 bath
Aug 21 – 26
Top guest favorite
Home in Shelter Island
Huge yard with beach a bike away
4.93 out of 5 average rating, 86 reviews, 4 bedrooms, 5 beds, 2 baths
Aug 13 – 18
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
Rooms in Shelter Island
Private cottage with a double whirlpool
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 1 bed, 1 bath
Aug 18 – 23
Guest favorite
Home in Shelter Island
Walk to Crescent Beach on Shelter Island
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 8 – 13
Superhost
Home in East Marion
Architect-designed bungalow on the bay
2 bedrooms, 2 beds, 1.5 baths
Sep 22 – 27
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
Top guest favorite
Home in Shelter Island
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
Home in Greenport
Newly renovated, one block from the village
4.95 out of 5 average rating, 266 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 12 – 17