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Search results; Over 1,000 homes in Shelter Island

Descriptions are based on details hosts provide
Top guest favourite
Home in Shelter Island Heights
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 private bathrooms
22–27 Sept
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4.91 out of 5 average rating, 93 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Place to stay in Shelter Island
Shelter Island retreat with private entrance
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 142 reviews
Guest favourite
Home in Shelter Island
Farmhouse with a pool and hammock
6 bedrooms, 3 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Shelter Island
New build with pool and beach access
3 bedrooms, 5 beds, 3 bathrooms
15–20 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Room in Shelter Island Heights
1800s farmhouse with a fire pit
1 king bed, 1 bathroom
15–20 Jul
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Cottage in Shelter Island
Tennis courts across the street, 4 bikes
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.97 out of 5 average rating, 120 reviews
Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
4 bedrooms, 5 beds, 2.5 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Shelter Island Heights
Private Hay Beach Retreat with Heated Pool
4 bedrooms, 5 beds, 3 bathrooms
3–10 Aug
4.98 out of 5 average rating, 93 reviews
Top guest favourite
Home in Shelter Island Heights
Huge yard with beach a bike away
4 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
4.93 out of 5 average rating, 84 reviews
Guest favourite
Cottage in Shelter Island Heights
Bayfront cottage on a historic estate
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 76 reviews
Guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
1 king bed, 1 bathroom
9–14 Aug
4.83 out of 5 average rating, 42 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds, 2 bathrooms
23–30 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Rooms in Shelter Island
Porch overlooking an 8-acre reserve
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 48 reviews
Home in Shelter Island Heights
Private Shelter Island Escape | Huge Yard + Pool
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Home in Shelter Island Heights
Heated saltwater pool on Shelter Island
3 bedrooms, 3 beds, 2 bathrooms
20–27 Sept
5.0 out of 5 average rating, 74 reviews
Top guest favourite
Cottage in Shelter Island Heights
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.93 out of 5 average rating, 27 reviews
Guest favourite
Home in Shelter Island Heights
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 74 reviews