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Search results; Over 1,000 homes in Shelter Island

Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 private bathroom
4–9 Aug
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4.99 out of 5 average rating, 74 reviews
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
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
30 Aug – 4 Sept
Guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
4.84 out of 5 average rating, 44 reviews, 1 king bed, 1 bathroom
9–14 Aug
Top guest favourite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
4.98 out of 5 average rating, 52 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Room in Shelter Island
A room in a sunny cottage with use of pool.
4.95 out of 5 average rating, 147 reviews, 1 king bed, 1 bathroom
1–6 Oct
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 1 bed, 2 bathrooms
13–18 Sept
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
4.95 out of 5 average rating, 166 reviews, 1 king bed, 1 bathroom
21–26 Aug
Top guest favourite
Home in Shelter Island
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
Home in Shelter Island
Private Shelter Island Escape | Huge Yard + Pool
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
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
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
Stunning water views, huge pool, family resort
4.93 out of 5 average rating, 57 reviews, 4 bedrooms, 6 beds, 3 bathrooms
2–7 Sept
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
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Room in Shelter Island
Candlelite Inn Queen Onsuite Bath
4.91 out of 5 average rating, 46 reviews, 1 queen bed, 1 bathroom
11–16 Aug
Apartment in Greenport
Water front, sunsets, sail boats, 30 day minimum
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Home in Shelter Island
Private Island retreat, beach and nature nearby !
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
4.84 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 1 bathroom
13–18 Sept