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Search results; Over 1,000 homes in Shelter Island

Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds, 2 private bathrooms
20–27 Sept
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5.0 out of 5 average rating, 75 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
6–11 Sept
4.95 out of 5 average rating, 41 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
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds
9–14 Aug
4.99 out of 5 average rating, 74 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds
7–12 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 122 reviews
Top guest favourite
Home in Shelter Island
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
9–14 Aug
4.92 out of 5 average rating, 13 reviews
Guest favourite
Cottage in Shelter Island
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds
10–15 Aug
4.93 out of 5 average rating, 27 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds
14–19 Aug
4.92 out of 5 average rating, 95 reviews
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds
13–18 Sept
4.84 out of 5 average rating, 76 reviews
Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds
2–7 Sept
4.93 out of 5 average rating, 44 reviews
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed
21–26 Aug
4.95 out of 5 average rating, 167 reviews
Top guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
1 king bed
9–14 Aug
4.84 out of 5 average rating, 44 reviews
Guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds
4–9 Oct
4.95 out of 5 average rating, 75 reviews
Top guest favourite
Home in Shelter Island
Private Hay Beach Retreat with Heated Pool
4 bedrooms, 5 beds
3–10 Aug
4.98 out of 5 average rating, 93 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds
5–12 Aug
Guest favourite
Room in Shelter Island
A room in a sunny cottage with use of pool.
1 king bed
1–6 Oct
4.95 out of 5 average rating, 147 reviews