THE PRIDWIN HOTEL, Shelter Island

The Pridwin Hotel - A waterfront resort with private cottages, seasonal water sports, and a spa

This 4-star waterfront resort on Shelter Island offers hotel rooms and private cottages with air conditioning, en-suite bathrooms, and free toiletries. Accommodations include Hillside Rooms with garden views, Waterview Rooms overlooking Crescent Beach, and cottages like Birch and White Oak featuring kitchenettes, gas fireplaces, and private decks. The Terrace restaurant serves a plated breakfast daily and offers Long Island cuisine with local oysters, striped bass, and prime NY strip steak. Guests at The Pridwin Hotel can access two docks with complimentary kayaks and paddleboards, a heated outdoor pool with beach views, tennis and pickleball courts, and a fitness center. The Pridwin Spa provides massages, facials, and body treatments using OSEA Malibu products. Ferry service connects Shelter Island from Greenport and Sag Harbor, with the property located 56 miles from Long Island MacArthur Airport. Complimentary high-speed WiFi is available throughout the grounds and accommodations.

Pros

Seasonal complimentary use of kayaks, paddleboards, and bicycles for guests

Heated outdoor pool with direct views of Crescent Beach and complimentary towels

Private cottages include kitchenettes, gas fireplaces, and decks with water views

On-site spa offers massages, facials, and full body treatments using organic products

Daily plated breakfast served at the waterfront Terrace restaurant

Cons

Ferry transportation required to access Shelter Island from mainland areas

Seasonal amenities like pool and water sports are unavailable during off-peak months