Places to Stay

Shelter Island offers a variety of guest houses, cabins, hotels, and marinas.
Each offers something unique either in atmosphere or facilities.
All are bustling in the summer and a few provide accomodations in the winter.

Bed and Breakfast

Azalea House
1 Thomas Avenue
Open year-round

Beach House
Open year-round 

Beech Tree House
1 South Ferry Road
Open year-round

Belle Crest House
163 North Ferry Road
Open year-round.

Candlelite Inn & Guest House
3 South Ferry Road
Open year-round

House on Chase Creek
3 Locust Avenue 

Lake Drive House Bed and Breakfast  
11 Lake Drive

Shelter Island Bed and Breakfast

Stearns Point House

Two South Ferry Road





















Chequit Inn
23 Grand Avenue - Heights
Full renovated rooms with private baths. Open year-round and 7 days a week for lunch and dinner.

Dering Harbor Inn
13 Winthrop Road
May - October, 2 night minimum. Cooperative apartments also available for weekly and seasonal rentals. Pool, tennis, and dockage for guests. On Shore restaurant.

Pridwin Resort Hotel
81 Shore Road
The beach of this resort is on Shelter Island Bay. There are 40 rooms and 9 heated efficiency apartments. Swimming pool, tennis courts, game room, docking and boat rental for guests. Diningroom and cocktail lounge.

Ram’s Head Inn
108 Ram Island Drive
This lovely old country inn has 17 rooms overlooking Coecles Harbor and Gardiner’s Bay. There are a restaurant, cocktail lounge, and lovely verandas for eating and drinking. Babysitting is available. Open year-round.

Shelter Island Hideaway European Elegance. 3 Bedrooms En-Suite. 20x40 Pool, 500 yards from waterfront. Featuring 3 bedrooms and 3 baths this home was designed and built by the editor of an international travel publication. All the bedrooms are en-suite with jetted Jacuzzi tubs and separate showers. There is an additional loft area with a couch bed too.

















Shelter Island House
11 Stearns Point Road
Fax 631-749-9321

This intimately sized hotel boasts graciously sized rooms, spa bathrooms, chic décor and local art. Complimentary amenities, including continental breakfast, Wi-Fi, pool, an on premises bakery, restaurant and bar are just a glimpse of what is provided to enhance your experience while visiting our boutique hotel.

Sunset Beach Hotel
35 Shore Road
Overlooking Shelter Island Bay on Crescent Beach, Sunset Beach is a lively 20 room hotel with a popular French beachside restaurant. Every room has a private terrace and bay views.

For Visitors on Boats

Coecles Harbor Marina
Hudson Street
In magnificent Coecles Harbor, 40 moorings and 55 slips. Head, showers, ice, beverages, snack bar, laundry, swimming pool, and gift shop. Boat repair, maintenance, and storage.

Dering Harbor Marina
Bridge Street - Heights 
Twenty-five slips. Head, shower, fuel, groceries, ice, laudromat, restaurants, bike rental, and free shuttle service to beach.

The Island Boatyard & Marina
South Menantic Road
A brand-new full service marina in beautiful Menantic Bay. Many slips, laundromat, ice, head and showers.

Jack’s Marine
Bridge Street
Full service marine supplies and docking.










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