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 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
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
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 29
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
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
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
Photo 1 of 28
Guest favourite
Home in Greenport
North Fork Sound Front Home with Pool
4 bedrooms, 4 beds, 4 bathrooms
1–6 Oct
4.87 out of 5 average rating, 46 reviews
Photo 1 of 29
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
1–8 Oct
Photo 1 of 29
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
Photo 1 of 22
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
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, 73 reviews
Photo 1 of 29
Home in Shelter Island
Shelter Island House with water views & cottage
5 bedrooms, 6 beds, 3 bathrooms
2–7 Oct
4.8 out of 5 average rating, 5 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 6
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
Photo 1 of 23
Guest favourite
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 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 29
Top guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds, 1 bathroom
12–17 Oct
4.97 out of 5 average rating, 172 reviews
Photo 1 of 29
Guest favourite
Home in Greenport
Corwin House
4 bedrooms, 4 beds, 3 bathrooms
12–18 Oct
4.99 out of 5 average rating, 68 reviews