Shelter Island holiday rentals
Find the best place to stay - Shelter Island
Gorgeous private Hamptons house with pool and volleyball court
Find spaces that suit your style
Top rated rentals - Shelter Island
Photo gallery for Private Coastal Two Bedroom Cottage on the Water
Lovely place right on a lake
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Scenic Shelter Island will entice you
The area's history and museums are just some of the reasons to come on holiday to Shelter Island. Travellers to this scenic city praise the island views, kayaking and parks. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.
Activities and attractions in and around Shelter Island
Are you searching for attractions to see in the area? Venture out of your holiday home and experience everything that makes Shelter Island a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:
- Greenport Carousel (2.6 mi / 4.2 km)
- Kontokosta Winery (3.5 mi / 5.7 km)
- Raphael Winery (6.8 mi / 10.9 km)
- Pindar Vineyards (7 mi / 11.3 km)
- Bedell Cellars (7.3 mi / 11.7 km)
- Peconic Bay Winery (8.1 mi / 13.1 km)
Exploring the natural features in Shelter Island
Whether you're an active traveller or just want to take in the scenery, Shelter Island is a great place to spend some time outside. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:
- Sunset Beach (1.5 mi / 2.4 km)
- Crescent Beach (1.7 mi / 2.8 km)
- 67 Steps Beach (4 mi / 6.4 km)
- Sag Harbor Marine Park (5.1 mi / 8.3 km)
- Orient Beach State Park (5.7 mi / 9.2 km)
- Orient Point County Park (8.1 mi / 13.1 km)
How to get to and around Shelter Island
The nearest airport is in East Hampton, NY (HTO), located 8.8 mi (14.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away.