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Search results; Over 1,000 homes in Shelter Island

Top 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, 43 reviews
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 149 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 128 reviews
Top guest favourite
Guest house in Shelter Island Heights
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 78 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Room in Shelter Island Heights
Master Suite at RedHouse
1 king bed, 1 bathroom
31 Aug – 5 Sept
4.95 out of 5 average rating, 168 reviews
Top guest favourite
Home in Shelter Island Heights
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 79 reviews
Top guest favourite
Home in Shelter Island Heights
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 bathrooms
9–16 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Shelter Island Heights
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
4.93 out of 5 average rating, 86 reviews
Guest favourite
Cottage in Shelter Island Heights
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.93 out of 5 average rating, 27 reviews
Top guest favourite
Home in Shelter Island Heights
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, 77 reviews
Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 44 reviews
Guest favourite
Guest house in Shelter Island Heights
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds, 2 bathrooms
17–22 Apr
5.0 out of 5 average rating, 25 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.92 out of 5 average rating, 13 reviews
Guest favourite
Cottage in Shelter Island Heights
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 80 reviews
Top guest favourite
Home in Shelter Island Heights
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.92 out of 5 average rating, 97 reviews
Top guest favourite
Guest suite in Shelter Island Heights
Chic and Cozy Suite with Private Entrance
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 56 reviews