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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, 263 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
13–20 Jul
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
8–13 Jul
5.0 out of 5 average rating, 8 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, 37 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
4.91 out of 5 average rating, 93 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
Room in Shelter Island
Magnolia Cape with private entrance & private bath
1 king bed, 1 bathroom
16–21 Jul
4.83 out of 5 average rating, 42 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
4.97 out of 5 average rating, 118 reviews
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
13–18 Jul
4.93 out of 5 average rating, 84 reviews
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
4.91 out of 5 average rating, 138 reviews
Superhost
Home in Greenport
Stylish Getaway in Greenport
3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
4.89 out of 5 average rating, 37 reviews
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
19–24 Jul
4.95 out of 5 average rating, 165 reviews
Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
4 bedrooms, 5 beds, 2.5 bathrooms
10–15 Jul
5.0 out of 5 average rating, 28 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, 75 reviews
Guest favourite
Home in Shelter Island
"Cozy Cove" Waterfront Home
2 bedrooms, 3 beds, 2 bathrooms
8–13 Jul
4.71 out of 5 average rating, 14 reviews
Guest favourite
Home in Shelter Island
Waterfront shelter island gem
4 bedrooms, 5 beds, 2.5 bathrooms
10–15 Jul
4.95 out of 5 average rating, 40 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, 73 reviews
Guest favourite
Rooms in Shelter Island Heights
SEVEN on Shelter - Luxury King w/ Private Bathroom
2 bedrooms, 1 king bed, 1 bathroom
18–23 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Greenport
Quaint Chalet w/Salt-heated Pool
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 12 reviews