Photo by tom owens

Luxury Hotels & Resorts in Shelter Island

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check availability on Shelter Island Luxury Hotels

Best Shelter Island Luxury Hotels

Top Shelter Island Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Good for passing by. "
Dynalee 1-night trip
Posted 4 days ago
Pier Blue Inn Old Saybrook - Essex

Frequently asked questions

Are you looking for a luxury hotel for your Shelter Island holiday?
Use Expedia to help you arrange a flight to East Hampton, NY (HTO) airport or Fishers Island, NY (FID-Elizabeth Field) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Shelter Island offers. Shelter Island has some interesting things to see and do including Sunset Beach and Crescent Beach, so you might want to take in the local sights during your visit.
When can I expect good weather in Shelter Island?
Planning for the weather is a good way to make your trip to Shelter Island relaxing and enjoyable, especially when you're splurging. The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island is 1452 mm.
What's there to see and do in Shelter Island?
Take in some sights and attractions while you're in Shelter Island by visiting Sunset Beach, Crescent Beach and Mashomack Preserve. If you have some spare time during your trip, you might want to check out Gardiner's Bay Country Club and Shelter Island Historical Society.

Explore a world of travel with Expedia