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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
1–6 Dec
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4.9 out of 5 average rating, 273 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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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
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
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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Top guest favourite
Home in Shelter Island
Shelter Island 4 BR w Pool & Private Beach Access
4 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
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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
20–25 Sept
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
30 Sept – 5 Oct
4.82 out of 5 average rating, 84 reviews
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Guest favourite
Home in Greenport
Restored Gem w/ Pool
4 bedrooms, 7 beds, 4.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 13 reviews
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Top guest favourite
Room in Shelter Island
Casual Island Getaway - Walk to the Beach
1 queen bed, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 162 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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Guest favourite
Villa in Greenport
Year-Round Heated Pool Villa - 3 blocks from town
4 bedrooms, 8 queen beds, 4.5 bathrooms
11–16 Oct
4.91 out of 5 average rating, 90 reviews
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Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
4 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
4.97 out of 5 average rating, 32 reviews
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Flat in Shelter Island Heights
5 star Waterfront cottage at Dering Harbor Inn.
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
New place to stay
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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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Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
20–27 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Greenport
North Fork Sound Front Home with Pool
4 bedrooms, 4 beds, 4 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 172 reviews
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Guest favourite
Home in Greenport
Walk to Beach or to Town …
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.89 out of 5 average rating, 44 reviews