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

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Superhost
Flat in Shelter Island Heights
Squire Chase House
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
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4.9 out of 5 average rating, 273 reviews
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Top guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 80 reviews
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Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 131 reviews
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 44 reviews
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Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct
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Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.91 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Shelter Island
Shelter Island home with pool
4 bedrooms, 6 beds, 2.5 bathrooms
19–24 Oct
4.96 out of 5 average rating, 73 reviews
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Guest favourite
Home in Shelter Island
Peaceful Bright Country House
3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
4 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Shelter Island
Shelter Island 4 BR w Pool & Private Beach Access
4 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 11 reviews
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Home in Shelter Island
Shelter Island House with water views & cottage
5 bedrooms, 6 beds, 3 bathrooms
2–7 Oct
4.8 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 77 reviews
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Featured hotel
Hotel in Greenport
King Suite
1 bedroom, 1 king bed, 1 bathroom
29 Sept – 4 Oct
New place to stay
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Top guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 172 reviews
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Top guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Greenport
Corwin House
4 bedrooms, 4 beds, 3 bathrooms
12–18 Oct
4.99 out of 5 average rating, 68 reviews
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Guest favourite
Flat in Greenport
Harbor Heights
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
4.94 out of 5 average rating, 247 reviews