filters

Search results; Over 1,000 homes in Shelter Island

Photo 1 of 26
Home in Shelter Island
Waterfront Haven
5 bedrooms, 9 beds, 4.5 private bathrooms
5–10 Oct
,
4.88 out of 5 average rating, 17 reviews
Photo 1 of 20
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
Photo 1 of 29
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
Photo 1 of 12
Featured hotel
Hotel in Greenport
King Suite
1 bedroom, 1 king bed, 1 bathroom
29 Sept – 4 Oct
New place to stay
Photo 1 of 29
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
Photo 1 of 16
Guest favourite
Home in Shelter Island
Peaceful Bright Country House
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 11 reviews
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
20–25 Sept
5.0 out of 5 average rating, 77 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, 154 reviews
Photo 1 of 29
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
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, 79 reviews
Photo 1 of 26
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 79 reviews
Photo 1 of 29
Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 23 reviews
Photo 1 of 6
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
Photo 1 of 24
Guest favourite
Home in Shelter Island
Family Friendly Modern Island Home Steps to Beach!
4 bedrooms, 7 beds, 3.5 bathrooms
18–23 Sept
4.93 out of 5 average rating, 15 reviews
Photo 1 of 29
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
21–26 Sept
New place to stay
Photo 1 of 18
Flat in Shelter Island Heights
5 star Waterfront cottage at Dering Harbor Inn.
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
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
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
Photo 1 of 25
Guest favourite
Home in Shelter Island
Shelter Island Retreat | 3 King Beds + Huge Yard
4 bedrooms, 5 beds, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 5 reviews
Photo 1 of 13
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
30 Sept – 5 Oct
4.82 out of 5 average rating, 84 reviews