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Search results; Over 1,000 homes in Shelter Island

Guest favourite
Home in Shelter Island
Hay Beach Family Home: Fire Pit, Playroom, Yard
3 bedrooms, 4 beds, 2 private bathrooms
19–24 Jul
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4.9 out of 5 average rating, 126 reviews
Guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 37 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, 23 reviews
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.91 out of 5 average rating, 136 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
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 8 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, 83 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, 91 reviews
Guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
4.94 out of 5 average rating, 72 reviews
Top guest favourite
Cottage in Shelter Island
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.93 out of 5 average rating, 27 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
13–20 Jul
New place to stay
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, 74 reviews
Top guest favourite
Rooms in Shelter Island
Grace House
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds, 2 bathrooms
25 Jul – 1 Aug
5.0 out of 5 average rating, 73 reviews
Guest favourite
Home in Shelter Island
Stunning water views, huge pool, family resort
4 bedrooms, 6 beds, 3 bathrooms
16–21 Jul
4.93 out of 5 average rating, 56 reviews
Top guest favourite
Home in Shelter Island
Private Hay Beach Retreat with Heated Pool
4 bedrooms, 5 beds, 3 bathrooms
3–10 Aug
4.98 out of 5 average rating, 92 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Aug
4.92 out of 5 average rating, 12 reviews
Guest favourite
Home in Shelter Island
Hamptons - Shelter Island Farmhouse
4 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
4.94 out of 5 average rating, 51 reviews
Guest favourite
Cottage in Shelter Island
Charming Coastal Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
4.84 out of 5 average rating, 44 reviews