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

Loft in Shelter Island Heights
Waterfront jewel box on a high bluff.
1 bedroom, 2 beds, 1 shared bathroom
1–8 Sept
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 42 reviews
Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 20 reviews
Home in Sag Harbor
Shelter Island Shell Beach Oasis
4 bedrooms, 5 beds, 3 bathrooms
17–22 Aug
New place to stay
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 128 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
29 Aug – 4 Sept
5.0 out of 5 average rating, 3 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
4.92 out of 5 average rating, 149 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 77 reviews
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 168 reviews
Top guest favourite
Home in Greenport
Dream Get Away
2 bedrooms, 2 king beds, 2.5 bathrooms
23–28 Aug
4.94 out of 5 average rating, 292 reviews
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
4.93 out of 5 average rating, 86 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Shelter Island
Peaceful Bright Country House
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 11 reviews
Superhost
Home in East Marion
Bungalow by the Bay
2 bedrooms, 2 queen beds, 1.5 bathrooms
22–27 Sept
Guest favourite
Home in Shelter Island
Mid-Century Gem with Pool. Steps to Private Beach.
3 bedrooms, 3 beds, 2.5 bathrooms
7–14 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Cottage in Shelter Island
Charming Coastal Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
4.85 out of 5 average rating, 47 reviews
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 99 reviews
Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds, 2 bathrooms
17–24 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Greenport
Aqua Vista
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 268 reviews