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Search results; Over 1,000 homes in Shelter Island

Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 private bathrooms
6–11 Sept
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4.97 out of 5 average rating, 124 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, 143 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds
7–12 Sept
4.99 out of 5 average rating, 76 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, 45 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, 168 reviews
Top guest favourite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
1 bedroom, 1 bed
2–7 Aug
4.98 out of 5 average rating, 53 reviews
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
2 bedrooms, 1 bed
13–18 Sept
4.96 out of 5 average rating, 26 reviews
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
Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds
8–13 Nov
4.93 out of 5 average rating, 44 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
Guest favourite
Rooms in Shelter Island Heights
SEVEN on Shelter - Luxury King w/ Private Bathroom
2 bedrooms, 1 king bed
3–8 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds
9–14 Aug
4.92 out of 5 average rating, 13 reviews
Apartment in Shelter Island Heights
Shelter Island Waterview Villa
1 bedroom, 2 beds
1–6 Aug
5.0 out of 5 average rating, 3 reviews
Home in Shelter Island
Private Island retreat, beach and nature nearby !
3 bedrooms, 4 beds
2–7 Aug
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
Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds
20–27 Sept
5.0 out of 5 average rating, 75 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, 85 reviews
Guest favourite
Room in Shelter Island
Candlelite Inn Queen Onsuite Bath
1 queen bed
18–23 Aug
4.91 out of 5 average rating, 46 reviews
Guest favourite
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds
24–29 Aug
5.0 out of 5 average rating, 5 reviews