filters

Search results; Over 1,000 homes in Shelter Island

Photo 1 of 6
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 private bathroom
1–6 Oct
,
4.97 out of 5 average rating, 79 reviews
Photo 1 of 6
Top guest favourite
Room in Shelter Island
Casual Island Getaway - Walk to the Beach
1 queen bed, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 162 reviews
Photo 1 of 29
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 45 reviews
Photo 1 of 29
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, 80 reviews
Photo 1 of 29
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 131 reviews
Photo 1 of 27
Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.93 out of 5 average rating, 45 reviews
Photo 1 of 28
Top guest favourite
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 bathrooms
1–8 Oct
5.0 out of 5 average rating, 14 reviews
Photo 1 of 6
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, 155 reviews
Photo 1 of 29
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
New place to stay
Photo 1 of 21
Guest favourite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
4 bedrooms, 4 beds, 3 bathrooms
2–7 Oct
5.0 out of 5 average rating, 22 reviews
Photo 1 of 29
Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds, 2 bathrooms
22–27 May
5.0 out of 5 average rating, 27 reviews
Photo 1 of 29
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
1–8 Oct
Photo 1 of 29
Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 77 reviews
Photo 1 of 13
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
1–6 Oct
4.82 out of 5 average rating, 84 reviews
Photo 1 of 29
Guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds, 1 bathroom
12–17 Oct
4.97 out of 5 average rating, 172 reviews
Photo 1 of 6
Guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 174 reviews
Photo 1 of 16
Guest favourite
Home in Shelter Island Heights
Gingerbread Cottage
5 bedrooms, 6 beds, 4.5 bathrooms
2–9 Oct
5.0 out of 5 average rating, 11 reviews
Photo 1 of 16
Guest favourite
Home in Shelter Island
Peaceful Bright Country House
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 11 reviews
Photo 1 of 15
Featured hotel
Hotel in Greenport
Oyster Estate, Corner king
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
New place to stay