The Pridwin Hotel and Cottages
The Pridwin Hotel and Cottages is a classic American resort hotel that has been providing guests a unique experience on Shelter Island since 1927. Located just a five-minute ferry ride from The Hamptons, luxurious amenities and waterfront views intertwine at this incredible Shelter Island property. Unwind in elegant rooms or private cottages, rejuvenate at The Spa, and savor cuisine with stunning water views at The Terrace.
The Pridwin's 33 rooms and 16 cottages blend the resort's original 1920s charm with fresh, playful details like bold wallpapers, antique wicker, and vibrant fabrics. Private studio and two-bedroom cottages evoke a summer-camp feel, offering relaxed, refined stays with stunning Peconic Bay views.
Each morning at The Pridwin begins with a complimentary continental breakfast featuring an omelette station, fresh pastries, seasonal fruit, cereals, yogurt, coffee, and seasonal accompaniments. On-property dining options include The Terrace, where fresh seafood and seasonal ingredients meet stunning water views. The iconic Crescent Bar serves a range of classic cocktails and new twists, while the Osprey Nest bar offers poolside bites and refreshments. From casual lunches to elegant dinners, every meal at The Pridwin captures the relaxed charm of Shelter Island dining. Guests are also welcome to savor the flavors of The Pridwin from the comfort of their room with our convenient room service. Whether it's afternoon snacks or dinner a private cottage deck, guests can enjoy chef-prepared meals delivered right to their door for a truly indulgent experience.
The Pridwin Hotel and Cottages elevates the island retreat experience with luxurious amenities, including a heated waterfront pool, full‑service spa, and wellness center. Guests enjoy tennis and pickleball courts, curated lawn games, bikes, fishing, kayaks, paddleboards, and concierge services—crafting an indulgent yet effortlessly relaxed Shelter Island escape.
Travel to The Pridwin is a breeze. Reaching hotel is part of the experience—an effortless journey to a world apart. A scenic drive leads to the Shelter Island Ferry; a brief, charming crossing that feels more like a prelude to escape than transit. In minutes, guests arrive at our tranquil, luxurious waterfront retreat.
Hotel Amenities
From waterfront dining with stunning views to thrilling social events that put local cuisine at the forefront, every culinary experience at The Pridwin Hotel and Cottages captures the magic of the region.
- The TerraceCuisine Type: American (Lunch and Dinner) • Capacity: 125The Crescent BarCuisine Type: Cocktails and Light Bites • Capacity: 35The Osprey Nest Pool BarCuisine Type: Cocktails and Light Bites • Capacity: 25
- Seasonal DiningCuisine Type: American • Capacity: 350
- The TerraceCuisine Type: American (Lunch and Dinner) • Capacity: 125The Crescent BarCuisine Type: Cocktails and Light Bites • Capacity: 35
- The Osprey Nest Pool BarCuisine Type: Cocktails and Light Bites • Capacity: 25Seasonal DiningCuisine Type: American • Capacity: 350
- The TerraceCuisine Type: American (Lunch and Dinner) • Capacity: 125
- The Crescent BarCuisine Type: Cocktails and Light Bites • Capacity: 35
- The Osprey Nest Pool BarCuisine Type: Cocktails and Light Bites • Capacity: 25
- Seasonal DiningCuisine Type: American • Capacity: 350
This Fall and Spring, enjoy reduced fees and a complimentary welcome hour when you book a midweek group retreat.
This fall and spring, The Pridwin Hotel and Cottages invites your group to gather on ten acres of serene Shelter Island waterfront for meaningful connection and collaboration. With site fees and resort fees waived, planners can focus on crafting experiences that truly matter—fostering camaraderie, creativity, and growth.
Host your welcome hour with craft beers, select wines, and artisanal cheeses in a setting of your choice: The Grove beneath the trees, the water-view Lawn, or one of our inviting indoor spaces. Between sessions, enjoy team-building activities like croquet, pickleball, kayaking, or guided hikes through the nearby Mashomack Preserve, all designed to inspire connection in a naturally restorative setting.
Plan a Spring or Fall Group Retreat and Enjoy:*
- Complimentary Welcome Hour in a location of your choice, featuring beer, wine, artisanal cheeses, and one additional appetizer station
- Waived Resort Fee (midweek only)
- Reduced Site Fees (midweek only)
*Subject to availability and change. Offer applies to groups with 20 rooms for 2 or more nights with a minimum of 40 room nights. Must include a stay midweek on a Sunday, Monday, Tuesday, and/or Wednesday night. Offer does not apply to existing group reservations, blocks, or master folios. Cannot be combined with other packages or offers.