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Search results; Over 1,000 homes in Shelter Island

Guest favourite
Home in Shelter Island Heights
Hay Beach Family Home: Fire Pit, Playroom, Yard
3 bedrooms, 4 beds, 2 private bathrooms
26–31 Jul
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4.9 out of 5 average rating, 128 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
9–14 Aug
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 bedroom, 1 queen bed
4–9 Oct
4.92 out of 5 average rating, 142 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds
18–23 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds
2–7 Aug
4.97 out of 5 average rating, 122 reviews
Top guest favourite
Home in Shelter Island Heights
Family Friendly Island Home
4 bedrooms, 5 beds
10–15 Aug
4.93 out of 5 average rating, 84 reviews
Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds
23–30 Aug
5.0 out of 5 average rating, 24 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds
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
9–14 Aug
4.83 out of 5 average rating, 42 reviews
Top guest favourite
Room in Shelter Island Heights
Master Suite at RedHouse
1 king bed
19–24 Jul
4.95 out of 5 average rating, 166 reviews
Guest favourite
Cottage in Shelter Island Heights
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds
13–18 Sept
4.84 out of 5 average rating, 76 reviews
Home in Shelter Island Heights
Private Shelter Island Escape | Huge Yard + Pool
4 bedrooms, 5 beds
9–14 Aug
Top guest favourite
Home in Shelter Island Heights
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds
23–28 Jul
4.91 out of 5 average rating, 94 reviews
Top guest favourite
Cottage in Shelter Island Heights
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds
10–15 Aug
4.93 out of 5 average rating, 27 reviews
Guest favourite
Home in Shelter Island
Charming Farmhouse with Pool
6 bedrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Shelter Island Heights
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds
4–9 Oct
4.95 out of 5 average rating, 74 reviews
Top guest favourite
Home in Shelter Island Heights
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds
20–27 Sept
5.0 out of 5 average rating, 74 reviews
Guest favourite
Rooms in Shelter Island
Grace House
2 bedrooms, 2 beds
13–18 Sept
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Shelter Island Heights
Private Hay Beach Retreat with Heated Pool
4 bedrooms, 5 beds
3–10 Aug
4.98 out of 5 average rating, 93 reviews