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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, 271 reviews
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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, 43 reviews
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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, 129 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Sept
New place to stay
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Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 22 reviews
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Superhost
Home in Shelter Island
Light- filled historic home -walk to water-pool
6 bedrooms, 6 beds, 4 bathrooms
7–12 Sept
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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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Guest favourite
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 bathrooms
9–16 Sept
5.0 out of 5 average rating, 13 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, 79 reviews
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Superhost
Home in East Marion
Bungalow by the Bay
2 bedrooms, 2 queen beds, 1.5 bathrooms
28 Sept – 3 Oct
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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, 155 reviews
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Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
4.96 out of 5 average rating, 178 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
13–18 Sept
4.91 out of 5 average rating, 89 reviews
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Guest favourite
Room in Shelter Island
A room in a sunny cottage with use of pool.
1 king bed, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 151 reviews
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Top guest favourite
Home in Shelter Island
Chic, serene, designer home with pool and views
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
4.98 out of 5 average rating, 44 reviews
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Guest favourite
Home in Greenport
Aqua Vista
2 bedrooms, 3 beds, 1 bathroom
29 Oct – 3 Nov
4.95 out of 5 average rating, 270 reviews
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Guest favourite
Home in Shelter Island
Shelter Island Retreat | 3 King Beds + Huge Yard
4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
1 king bed, 1 bathroom
13–18 Sept
4.86 out of 5 average rating, 49 reviews
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Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
20–25 Sept
5.0 out of 5 average rating, 100 reviews