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Search results; Over 1,000 homes in Shelter Island

Holiday home in Shelter Island
The Perfect Shelter Island Getaway! With Pool
3 bedrooms, 6 beds, 2.5 private bathrooms
27 Sept – 2 Oct
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5.0 out of 5 average rating, 4 reviews
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
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Sept
New place to stay
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
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
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
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
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
Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 45 reviews
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
Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds, 2 bathrooms
20–27 Sept
5.0 out of 5 average rating, 77 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
3–8 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
5–10 Oct
4.93 out of 5 average rating, 87 reviews
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, 8 reviews
Home in Shelter Island
Shelter Island - Modern 4 Bed Home Close to Beach
4 bedrooms, 4 beds, 3 bathrooms
9–14 Sept
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
Superhost
Home in Shelter Island
Light- filled historic home -walk to water-pool
6 bedrooms, 6 beds, 4 bathrooms
7–12 Sept
Top guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 172 reviews
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 83 reviews