Waterfront Hambleton Inn Bed & Breakfast

Nestled by the marina, St. Michaels Harbor Inn offers nautical-themed rooms, a spa, and a vibrant outdoor pool, all just a stroll from charming shops and eateries.

Charming, old-fashioned ice cream parlor with a huge menu of creative shakes & sundaes.

19th-century manor house with elegant rooms & suites, plus a spa, al fresco dining & event space. Set in a colonial-style, 19th-century manor house, this luxe riverside hotel in Saint Michaels is half a mile from the Chesapeake Bay Maritime Museum. Elegant rooms and suites come with antique-style furnishings. Many feature private patios or balconies; all have WiFi access and flat-screen TVs. Dining options include a waterside restaurant with afternoon tea, and a cozy pub with a fireplace. Other amenities include event space, an outdoor pool, a spa and fitness center, and free bike rental. Boat trips are also available (fee).

Charming bistro serving classic Italian fare such as pasta, pizzas & risotto, plus wine & spirits.

LYON RUM is the flagship product of Windon Distilling, located in Saint Michaels, Maryland, steps from the Chesapeake Bay. Founded in 2012, the distillery launched on 12/7/13 with a signature line of rums paying tribute to the rich, spirited traditions of the Eastern Shore. LYON spirits start with intentionally-sourced raw ingredients, and are truly hand-crafted - mashed, fermented, and double-distilled in small pot stills - every step of the way, resulting in a superior and unique final product. The goal is to create distinctly American spirits - working to define the category of New American Rum, while experimenting with obscure and varied finishes. Every spirit passes through the hands, and discerning palates, of the LYON RUM team.

Local pub serving hearty American fare in a laid-back setting with a model train, pool & live music.

Casual landmark crab shack offering regional seafood with outdoor tables & views of the Miles River.

Chic space with stunning river views serves a seasonal American menu and lovely afternoon tea, perfect for a special occasion or weekend brunch.

Hopping riverfront spot with a patio offering seafood eats, local craft beer on tap & live music.

New American mainstay providing a market-fresh menu with gluten-free options in a romantic setting.