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153 properties in and around Shelter Island

Shelter IslandShow on map1.9 miles from centre
This property boasts a private beach area, spa facilities, swimming pool with a view, and tennis court.
Shelter IslandShow on map3.2 miles from centre
This spacious holiday home offers beachfront access, an outdoor swimming pool, and a wellness centre.
Shelter Island HeightsShow on map1.2 miles from Shelter Island
An adults-only retreat offering a fitness centre, year-round outdoor swimming pool, and sun terrace.
Shelter Island HeightsShow on map1.2 miles from Shelter Island
This property boasts a seasonal outdoor swimming pool, sun terrace, restaurant, and bar for relaxation.
GreenportShow on map2.6 miles from Shelter Island
Beachfront hotel with a swimming pool, fitness centre, and private check-in & check-out services.
GreenportShow on map2.6 miles from Shelter Island
Offering a sun terrace, free use of bicycles, and private check-in services for ultimate convenience.
GreenportShow on map2.6 miles from Shelter Island
Offering a private beach area, beachfront access, and a family-friendly restaurant with outdoor seating.
GreenportShow on map2.9 miles from Shelter Island
This spacious apartment offers air-conditioning, a fully equipped kitchen, and paid on-site parking.
Shelter Island HeightsShow on map1.2 miles from Shelter Island
Offering a serene garden and terrace, this property provides free on-site private parking and air-conditioning.
Shelter Island HeightsShow on map1 miles from Shelter Island
Housed in a historic building, this guest house offers free use of bicycles and beautiful gardens.
GreenportShow on map2.7 miles from Shelter Island
Housed in a historic building, this property offers free use of bicycles, a restaurant, and bar.
GreenportShow on map2.7 miles from Shelter Island
Offering a sun terrace, garden, and free use of bicycles, this property ensures delightful stays.
GreenportShow on map2.8 miles from Shelter Island
This apartment offers a spa and wellness centre, air-conditioning, and a convenient location.
GreenportShow on map2.6 miles from Shelter Island
This spacious holiday home offers a restaurant and an inviting outdoor seating area for relaxation.
GreenportShow on map2.8 miles from Shelter Island
This spacious holiday home boasts a sauna, outdoor swimming pool, and inviting outdoor seating area.
GreenportShow on map2.5 miles from Shelter Island
This property boasts a private beach area, beachfront access, seasonal outdoor swimming pool, and bar.
GreenportShow on map2.8 miles from Shelter Island
An apartment offering a spa and wellness centre, air-conditioning, and a private entrance.
GreenportShow on map2.7 miles from Shelter Island
Housed in a historic building, this property offers a sun terrace, garden, and bar amenities.
GreenportShow on map2.6 miles from Shelter Island
A luxurious retreat offering a spa and wellness centre, restaurant, hot tub, and room service.
New to Booking.com
East MarionShow on map4.1 miles from Shelter Island
Housed in a historic building, this adults-only retreat offers spa facilities, tennis court, and garden.
SoutholdShow on map4.2 miles from Shelter Island
A sun terrace and garden complement family rooms, outdoor seating, and free on-site parking.
GreenportShow on map3.2 miles from Shelter Island
Offering a garden, seasonal outdoor swimming pool, and family rooms for a delightful stay.
East HamptonShow on map5.6 miles from Shelter Island
Offering a pet-friendly camping experience with a family-friendly restaurant, outdoor fireplace, and karaoke.
GreenportShow on map3.4 miles from Shelter Island
Offering a private beach area, beachfront access, and a seasonal outdoor swimming pool for relaxation.
East MarionShow on map5 miles from Shelter Island
This spacious, adults-only holiday home offers beachfront access and a delightful on-site restaurant.