Top 5 Hotels in Sag Harbor & Shelter Island To Check Out

Rachel Feinblatt | November 2, 2020 | Lifestyle Travel


Two of the quaintest villages out East are also the perfect destination for a little fall getaway. With Sag's vibrant village life and Shelter Island's "away from it all" ambiance consider these hotels for your next visit. Here are 5 of the best hotels in Shelter Island and Sag Harbor to check out.



Sag Harbor's standout is Baron’s Cove, and its fall setlist is one you won’t want to miss from check-in to check-out. The current offering includes a weekend of eats curated by executive chef Nicholas Vogel and here is a little taste of it. Kick-off the weekend with a welcome dinner filled with awesome autumn eats, followed by delicious breakfast and lunch spreads. The ultimate wow meal will include multi-course, farm-to-table selections made by Vogel himself. With beautiful bay views, the ambiance and gourmandize galore your stay in one of the oldest whaling villages relaxing and full.

31 W. Water St., Sag Harbor,


As a unique and romantic getaway must, the Shelter Island Hotel is filled with historic references offset with modern touches. As one of the first hotels on Shelter Island, this hotel is located just steps away from the famous Sunset Beach, which sadly is closed for the season. Enjoy amenities including golf, tennis, beaches, and more, and be sure to stop at Osperey Bar & Grill for a specialty cocktail and a stellar wine list. Romantic and beautiful, this is one property worth the ferry trip.

11 Stearns Point Road, Shelter Island Heights,



Eight is enough, they say! And The American Hotel believes it. Sag's mainstay provides a unique, homey environment, with only eight rooms available making this hotel the hottest ticket! The beautiful rooms are filled with the finest American antiques and curious. The restaurant features an award-winning wine inventory and a menu perfect for hearty fare fans. Just steps away from awesome shops and bay-side spots, the proximity to Sag Harbor hotspots makes this hotel a pure winner.

49 Main St., Sag Harbor,


Looking for something even more intimate? The Shelter Island Hotel’s younger sister, the West Neck Guesthouse, provides guests with a cozier option. Each luxurious lodging has a king size bed and beach furnishings, and plenty of local charm. Its location cannot be beaten-- it is just a walking distance from Crescent beach and all of the shops and restaurants.

31 West Neck Rd., Shelter Island Heights,



Modern, fun, and light, SEVEN offers a different option for those who want to leave historic touches at their grandparents' house. With tons of activities from mini golf to hiking, this hidden gem will leave you with a fresh look at Shelter Island, that offers many amenities, outdoor activities, and a contemporary vibe.

7 Stearns Point Road, Shelter Island,

Photography by: American Hotel photo by Ian G Dagnall / Alamy Stock Photo, Photography courtesy of Baron's Cove, Lauren Kress Photography