The Best Relaxing weekend getaways in Chestertown, Maryland

Comfort Inn & Suites Chestertown is a cozy and welcoming lodging option located at 150 Scheeler Road in the charming town of Chestertown, Maryland, United States. This institution offers comfortable rooms and suites, modern amenities, and friendly service to ensure a pleasant stay for all guests. Whether you are visiting for business or pleasure, Comfort Inn & Suites Chestertown is the perfect choice for your accommodation needs. With its convenient location and warm hospitality, this institution is sure to provide a memorable experience for all travelers.

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.

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.

Courtyard Inn is a charming lodging establishment located at 6336 Church Hill Road in the picturesque town of Chestertown, Maryland. This cozy inn offers comfortable and well-appointed rooms, perfect for both leisure and business travelers. The Courtyard Inn provides a peaceful and relaxing atmosphere, making it an ideal place to unwind after a busy day exploring the nearby attractions or attending meetings in town. Guests can enjoy the convenience of being just a short drive away from local shops, restaurants, and historical sites. Whether you are visiting Chestertown for business or pleasure, Courtyard Inn offers a welcoming and hospitable environment for all guests.