filters

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

Photo 1 of 13
Superhost
Flat in Shelter Island Heights
Squire Chase House
3 bedrooms, 3 beds, 2 bathrooms
1–6 Dec
,
4.9 out of 5 average rating, 273 reviews
Photo 1 of 15
Featured hotel
Hotel in Greenport
Oyster Estate, Classic king
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
New place to stay
Photo 1 of 6
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
Photo 1 of 21
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, 22 reviews
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 29
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
15–22 Sept
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
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
Photo 1 of 24
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, 89 reviews
Photo 1 of 29
Top guest favourite
Home in Shelter Island
Chic, serene, designer home with pool and views
4 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.98 out of 5 average rating, 44 reviews
Photo 1 of 18
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
Photo 1 of 29
Home in Shelter Island Heights
Spacious beach house with stunning water views.
5 bedrooms, 8 beds, 4 bathrooms
4–11 Oct
5.0 out of 5 average rating, 11 reviews
Photo 1 of 6
Guest favourite
Room in Shelter Island
Candlelite Inn Queen Onsuite Bath
1 queen bed, 1 bathroom
1–6 Oct
4.92 out of 5 average rating, 51 reviews
Photo 1 of 29
Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 23 reviews
Photo 1 of 29
Top guest favourite
Home in Shelter Island
Family Friendly Oasis Steps to Water - Heated Pool
6 bedrooms, 9 beds, 3 bathrooms
1–6 Dec
5.0 out of 5 average rating, 46 reviews
Photo 1 of 29
Guest favourite
Home in Shelter Island
Moonlit Manor | Shelter Island Escape w/ Sauna
3 bedrooms, 3 beds, 2 bathrooms
3–10 Oct
4.94 out of 5 average rating, 18 reviews
Photo 1 of 29
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
New place to stay
Photo 1 of 13
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
Photo 1 of 29
Top guest favourite
Home in Shelter Island
Shelter Island home with pool
4 bedrooms, 6 beds, 2.5 bathrooms
19–24 Oct
4.96 out of 5 average rating, 74 reviews