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Search results; Over 1,000 homes in Shelter Island

Top guest favourite
Guest house in Shelter Island Heights
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 private bathroom
1–6 Aug
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4.99 out of 5 average rating, 74 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 40 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
4.92 out of 5 average rating, 142 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
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
1–6 Aug
Top guest favourite
Home in Shelter Island Heights
Family Friendly Island Home
4.93 out of 5 average rating, 84 reviews, 4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
4.97 out of 5 average rating, 122 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Home in Shelter Island Heights
Surf Scoter Cottage Shelter Island
4.91 out of 5 average rating, 94 reviews, 4 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
Home in Shelter Island Heights
Private Shelter Island Escape | Huge Yard + Pool
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
Guest favourite
Cottage in Shelter Island Heights
Waterfront Getaway on Shelter Island
4.93 out of 5 average rating, 27 reviews, 3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5.0 out of 5 average rating, 24 reviews, 5 bedrooms, 5 beds, 2 bathrooms
23–30 Aug
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
Top guest favourite
Room in Shelter Island Heights
Master Suite at RedHouse
4.95 out of 5 average rating, 166 reviews, 1 king bed, 1 bathroom
21–26 Aug
Guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
4.84 out of 5 average rating, 43 reviews, 1 king bed, 1 bathroom
9–14 Aug
Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
4.93 out of 5 average rating, 44 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Sept
Guest favourite
Home in Shelter Island
Charming Farmhouse with Pool
5.0 out of 5 average rating, 8 reviews, 6 bedrooms, 3 bathrooms
1–6 Aug
Top guest favourite
Home in Shelter Island Heights
CASA GYPSEA - a chic and peaceful 3 bedroom house
5.0 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 2 bathrooms
20–27 Sept
Guest favourite
Cottage in Shelter Island Heights
Large Waterfront Cottage on Historic Estate
4.84 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
Guest favourite
Home in Shelter Island Heights
Beautiful beach home with pool & water views!
4.95 out of 5 average rating, 75 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
Top guest favourite
Home in Shelter Island Heights
Private Hay Beach Retreat with Heated Pool
4.98 out of 5 average rating, 93 reviews, 4 bedrooms, 5 beds, 3 bathrooms
3–10 Aug