The Oak Bluffs Inn

The Cardboard Box offers a vibrant New American dining experience with a seafood twist, complemented by fabulous cocktails and lively weekend vibes.

At Red Cat Kitchen, you’ll find a cozy, art-filled space serving up creative, ever-changing New American dishes with a local twist, all just a hop from the ferry.

Chowder Company is a laid-back spot in Oak Bluffs known for its award-winning clam chowder, impressive lobster rolls, and a casual bar vibe with plenty of seafood options.

Upscale spot in a tranquil space with seasonal, area-sourced New American fare & an ample wine list.

Nestled by the water, Lookout Tavern serves up fresh New England seafood and burgers with creative cocktails, all while boasting stunning ocean views.

The Madison Inn, a cozy seaside gem in Oak Bluffs, is just minutes from the beach and ferry, offering bright rooms with beach gear and delightful snacks.

Nestled in Oak Bluffs, this welcoming, sandy beach features clear waters, vibrant morning meet-ups, and stunning sunrises, perfect for all visitors.

Nestled in a vibrant, historic building in Oak Bluffs, the Summercamp Hotel captures the charm of summer camp with chic rooms, harbor views, and a playful café.

Nestled between bustling Oak Bluffs and Edgartown, this relaxed resort boasts cozy studios with kitchens, a refreshing outdoor pool, and easy beach access.

Tony's Market in Oak Bluffs is a charming spot where you can munch on gourmet sandwiches, sip local beers, and stock up on fresh produce—all while basking in top-notch service.