Shelter Island vacation rentals
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Find the best place to stay - Shelter Island
Shelter Island Hidden Waterfront Gem
- 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, yards and more
- More for lessMore space, more privacy, more amenities — more value
Beautiful Shelter Island will entice you
The area's history and museums are just a few of the reasons to vacation in Shelter Island. Travelers to this scenic city praise the island views, kayaking and parks. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.
Activities and attractions in and around Shelter Island
Are you hoping to find things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Shelter Island has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:
- 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)
- Wolffer Estates Vineyard (9.1 mi / 14.6 km)
Exploring the natural features in Shelter Island
Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Shelter Island is a great place to get out in nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:
- 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)
- Elizabeth A. Morton National Wildlife Refuge (5.8 mi / 9.3 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 center. If you can't find a flight that works for your travel itinerary, you could book a flight to Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away.