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

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, 264 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 39 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4.91 out of 5 average rating, 93 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Aug
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
4.91 out of 5 average rating, 141 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
13–20 Jul
Home in Shelter Island
Captain Don’s Paradise
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
13–18 Jul
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
4.97 out of 5 average rating, 120 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4.93 out of 5 average rating, 84 reviews, 4 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Home in Shelter Island
Private Shelter Island Escape | Huge Yard + Pool
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
Guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
4.83 out of 5 average rating, 42 reviews, 1 king bed, 1 bathroom
19–24 Jul
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
4.95 out of 5 average rating, 165 reviews, 1 king bed, 1 bathroom
15–20 Jul
Top guest favourite
Home in Greenport
Greenport Gem
5.0 out of 5 average rating, 24 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
4.84 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
Superhost
Home in Greenport
Stylish Getaway in Greenport
4.89 out of 5 average rating, 37 reviews, 3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
Guest favourite
Home in Shelter Island
Waterfront shelter island gem
4.95 out of 5 average rating, 41 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
27 Aug – 3 Sept
Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
4.96 out of 5 average rating, 52 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug