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Search results; Over 1,000 homes in Shelter Island Heights

Guest favourite
Room in Shelter Island Heights
SEVEN on Shelter - Queen Room w/Private Bathroom
1 bedroom, 1 bed, 1 shared bathroom
20–25 Sept
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5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 22 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, 129 reviews
Superhost
Home in Shelter Island
Light- filled historic home -walk to water-pool
6 bedrooms, 6 beds, 4 bathrooms
9–14 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 22 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
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
4.92 out of 5 average rating, 159 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, 43 reviews
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
9–14 Sept
New place to stay
Guest favourite
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 bathrooms
9–16 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
11–16 Oct
5.0 out of 5 average rating, 102 reviews
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
11–16 Sept
4.96 out of 5 average rating, 179 reviews
Top guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms, 2 king beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 172 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
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct
Top guest favourite
Room in Shelter Island
Magnolia Cape with private entrance & private bath
1 king bed, 1 bathroom
13–18 Sept
4.86 out of 5 average rating, 50 reviews
Guest favourite
Home in Greenport
Walk to Beach or to Town …
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Sept
4.88 out of 5 average rating, 43 reviews
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.82 out of 5 average rating, 84 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