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Search results; Over 1,000 homes in Shelter Island

Top guest favourite
Home in Shelter Island
Newly Renovated w/ Pool, Hot tub & Fireplace
3 bedrooms, 5 beds, 2 private bathrooms
20–25 Sept
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4.91 out of 5 average rating, 35 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
4.93 out of 5 average rating, 161 reviews
Featured hotel
Hotel in Greenport
King Suite
1 bedroom, 1 king bed, 1 bathroom
29 Sept – 4 Oct
New place to stay
Top guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 172 reviews
Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 77 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 44 reviews
Guest favourite
Home in Shelter Island
Peaceful Bright Country House
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 131 reviews
Top guest favourite
Home in Shelter Island
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
Guest favourite
Room in Shelter Island
A room in a sunny cottage with use of pool.
1 king bed, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 154 reviews
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
21–26 Sept
New place to stay
Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Shelter Island
Shelter Island Retreat | 3 King Beds + Huge Yard
4 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 174 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.97 out of 5 average rating, 79 reviews
Guest favourite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
4 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Shelter Island
Family Friendly Modern Island Home Steps to Beach!
4 bedrooms, 7 beds, 3.5 bathrooms
16–21 Sept
4.93 out of 5 average rating, 15 reviews
Superhost
Home in Shelter Island
Light- filled historic home -walk to water-pool
6 bedrooms, 6 beds, 4 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct