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

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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
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 131 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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Flat in Shelter Island Heights
5 star Waterfront cottage at Dering Harbor Inn.
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
New place to stay
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Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
4.89 out of 5 average rating, 9 reviews
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Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
10–15 Nov
4.99 out of 5 average rating, 105 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
1–6 Oct
5.0 out of 5 average rating, 77 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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Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 32 reviews
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 45 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
1–6 Oct
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
1–6 Oct
4.82 out of 5 average rating, 84 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
New place to stay
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Guest favourite
Home in Greenport
Aqua Vista
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.95 out of 5 average rating, 271 reviews
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Top guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
1 king bed, 1 bathroom
1–6 Oct
4.86 out of 5 average rating, 51 reviews
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Guest favourite
Home in Greenport
Cosy North Fork Cottage with large backyard
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.98 out of 5 average rating, 166 reviews
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Guest favourite
Home in Greenport
The Sandpiper
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
4.95 out of 5 average rating, 397 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
1–6 Oct
5.0 out of 5 average rating, 21 reviews