Where To Stay: The Gallery Hotel
Quirky, colorful, and most importantly, comfortable, the Gallery Hotel is the place to stay in the area.The 10-room boutique hotel is easy to miss but, once inside, hard to forget. Located right on Main Street, it could pass as a gallery itself, or a funky cafe - both of which it technically contains. Full of art and kitschy finds, the multifaceted go-to even features a dreamy backyard garden as well as rooms with their own palm-filled sun decks. If the super-friendly staff and prime location don't get you, the decor definitely will. It felt like having a slumber party at Phoebe Buffay's place, and she's obviously our favorite character on Friends.
Gallery Hotel, 441 Main St, Greenport
[Photos via Gallery Hotel]