Family room decor in Chestertown, Maryland

Angela's Cottage is a charming store located at 335 High Street in Chestertown, Maryland. This quaint shop offers a variety of unique and handcrafted items, perfect for gifts or home decor. From handmade jewelry and pottery to locally sourced candles and artwork, Angela's Cottage has something for everyone. Step inside and browse through their collection of one-of-a-kind treasures, all while enjoying the cozy atmosphere of this inviting store. Whether you're looking for a special memento of your visit to Chestertown or a thoughtful present for a loved one, Angela's Cottage is the perfect place to find that special something.

BAD Alfred's Distilling is a unique institution located at 323 High Street in Chestertown, Maryland, United States. This brewpub and distillery offers house-made spirits, local craft beer, and delicious wood-fired pizzas. Established in 2018 by owners Al and Jennifer Cassinelli, Bad Alfred's continues to create small-batch craft spirits alongside an expanded cocktail, beer, and dining menu. Housed in a former historic garage and filling station, Bad Alfred's features an open and inviting dining room and bar that faces a glassed-in distillery space, allowing patrons to watch the spirit-making process while enjoying a drink, pizza, or live music. The back of the building has been transformed into a private event space with a bar, dining room, and conference space.

Great Oak Manor is a luxurious boutique hotel located in Chestertown, Maryland, overlooking the stunning Chesapeake Bay. With a focus on connection, reconnection, learning, and wellness, this institution offers exceptional experiences that make getaways truly memorable. The 12 comfortable rooms and suites, along with the expansive Carriage House Suite, are individually decorated and provide the perfect place to relax. Guests can enjoy a farm-to-table culinary experience crafted by the executive chef using ingredients from the garden and local farmers. Great Oak Manor is the perfect venue for corporate retreats, family gatherings, friends' weekends, and intimate weddings. With picturesque views, attention to detail, and friendly staff, this property is highly recommended for any occasion. Whether you are a discerning international traveler or someone looking for a relaxing getaway, Great Oak Manor will exceed your expectations and serve as your home away from home.

Welcome to Jellyfish Joel's Beach Bar, located at 22170 Great Oak Landing Road in Chestertown, Maryland, United States. Our bar is not just a place to grab a drink, but a destination for boaters and beach lovers alike. At Jellyfish Joel's, we take pride in caring for your boat with passion and attention to detail. Our newly renovated on-premise accommodations offer comfortable rooms with amenities such as a mini fridge, private bathroom, and access to ice & coffee stations. Guests can enjoy free parking, free Wi-Fi, and access to the beach, outdoor pool, golf course, and more during their stay. The Lodge is open year-round and conveniently located for local events.