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Search results; Over 1,000 homes in Shelter Island

Cottage in New York
Cozy Shelter Island 2 Bedroom 1 Bath Cottage
3 bedrooms, 5 beds, 1 private bathroom
27 Jul – 1 Aug
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4.94 out of 5 average rating, 51 reviews
Cottage in New York
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 40 reviews
Place to stay in New York
Casual Island Getaway - Walk to the Beach
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 142 reviews
Home in New York
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
21–26 Jul
5.0 out of 5 average rating, 8 reviews
Home in New York
Shelter Island House: Peaceful Retreat
3 bedrooms, 3 beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 28 reviews
Cottage in New York
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.97 out of 5 average rating, 122 reviews
Home in New York
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
4.93 out of 5 average rating, 84 reviews
Home in New York
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
4.91 out of 5 average rating, 94 reviews
Place to stay in New York
Master Suite at RedHouse
1 bedroom, 1 king bed, 1 bathroom
21–26 Aug
4.95 out of 5 average rating, 166 reviews
Bed and breakfast in New York
Magnolia Cape with private entrance & private bath
1 bedroom, 1 king bed, 1 bathroom
9–14 Aug
4.84 out of 5 average rating, 43 reviews
Guest house in New York
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
8–15 Aug
4.99 out of 5 average rating, 74 reviews
Home in New York
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds, 2 bathrooms
23–30 Aug
5.0 out of 5 average rating, 24 reviews
Home in New York
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
4.92 out of 5 average rating, 13 reviews
Cottage in New York
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 76 reviews
Home in New York
Private Shelter Island Escape | Huge Yard + Pool
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
Cottage in New York
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.93 out of 5 average rating, 27 reviews
Place to stay in New York
Grace House
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 48 reviews
Home in New York
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, 75 reviews
Home in New York
Family Friendly Oasis Steps to Water - Heated Pool
6 bedrooms, 9 beds, 3 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 41 reviews