Dering Harbor Inn

13 Winthrop Rd., Shelter Island, 11965, NY

Enter Your Trip Dates

1 Room / 2 Adults

1 rooms,
2 adults
  • Rooms:

  • Adults:

  • Close

TripAdvisor Rating


Located on 7 sprawling acres overlooking Shelter Island’s Dering Harbor, the Dering Harbor Inn is an idyllic seashore retreat. Families can choose from an assortment of spacious waterfront suites and villas depending on their needs. Abundant amenities include a beautifully situated outdoor heated pool, complimentary bicycles, picnic areas with barbecue grills, onsite yoga and fitness center, and a sandy beach.

Spend an hour or two with your book in one of the hotel’s many Adirondack chairs while the kids play on the lawns or rent kayaks, which can be delivered to the Inn. The Inn’s Dering Harbor location is ideal for taking a short stroll into the island’s main village for shopping and dining.

Our Editor Loves

  • Spacious, family friendly suites and villas
  • Pool, bicycles, and outdoor pool
  • Easy walk to the village for dining and shopping

Family Interests

  • Beach
  • Bicycling
  • Water Sports

Family Amenities

  • Family Room 5+
  • Pool


Fabulous Weekend

by ManhattanEscapist

We are two friends who were looking for a quick escape from New York City without a car. We found more than we could have hoped for in the Dering Harbor Inn. Travel from the city was easy, we took the LIRR and ferry there and the jitney back. The accommodations were exceptional. We had a a well appointed apartment with everything we could want. Shelly, the manager, was more than accommodating, informative, helpful and a sheer delight to deal with. Barbara also was extremely helpful by giving us suggestions for places to visit and restaurants. The view from our cabin was great, we had our morning coffee on the terrace. It was easy to get lost, because the streets were anything but grid like and in some intersections there was no clarity about which way to go.

Dering Harbor Inn is a Winner!

by Hockypuk

Just came home from my 2nd stay at Dering Harbor Inn with my wife. Besides the breathtaking view of the harbor, the rooms are more than adequate. While the unit we stayed in was not modern (in case that matters to you) it did have a 'beachy' charm about it. There was a decent sized TV, air conditioning, a kitchen area, a little bar area, chairs on the porch overlooking the harbor and most of all, the room and bathroom area was very clean. Kudos to the housekeeping crew! Sherry & Barbara at the front desk treated us very nice. They gave us tips on how to enjoy our visit to Shelter Island like where to park for the fireworks show, which restaurants had the best food, which beaches were the nicest, etc. They were extremely patient and kind. Great customer service. I would stay at Dering on my next visit to Shelter Island.