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Search results; Over 1,000 homes

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Superhost
Home in Shelter Island
Light- filled historic home -walk to water-pool
6 beds
21–26 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Shelter Island
Private Hay Beach Retreat with Heated Pool
5 beds
25–30 Oct
4.98 out of 5 average rating, 94 reviews
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Top guest favourite
Home in Shelter Island
Chic, serene, designer home with pool and views
10-min drive
21–26 Sept
4.98 out of 5 average rating, 44 reviews
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Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
10-min drive
18–23 Sept
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Shelter Island
Family Friendly Island Home
10-min drive
5–10 Oct
4.93 out of 5 average rating, 88 reviews
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Guest favourite
Home in Shelter Island
Shelter Island Family Friendly Home with Pool!
10-min drive
20–25 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 beds
4–9 Oct
4.97 out of 5 average rating, 30 reviews
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Guest favourite
Flat in Greenport
Amazing Greenport Village Apartment in CENTER!
7 beds
4–9 Oct
4.8 out of 5 average rating, 367 reviews
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Home in Shelter Island
60's Ranch meets the Mediterranean
10-min drive
1–6 Jun
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
20-min drive
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Greenport
Pennington House
3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Home in Greenport
Relaxation in Greenport
4 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 51 reviews
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Flat in Shelter Island Heights
5 star Waterfront cottage at Dering Harbor Inn.
10-min drive
20–25 Sept
New place to stay
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Top guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
4 beds
4–9 Oct
4.91 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
40-min drive
18–23 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Greenport
Walk to Beach or to Town …
4 beds
4–9 Oct
4.89 out of 5 average rating, 44 reviews
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Superhost
Home in East Marion
Bungalow by the Bay
2 queen beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Greenport
Luxurious Fully Renovated 1880's Farmhouse
12 beds
18–23 Sept
5.0 out of 5 average rating, 5 reviews