Motel in Chestertown, Maryland

Red Roof Inn & Suites Chestertown is a cozy and comfortable lodging option located at 160 Scheeler Road in Chestertown, Maryland, United States. This charming inn offers a variety of rooms and suites to accommodate guests, whether they are traveling for business or pleasure. The convenient location provides easy access to local attractions, restaurants, and shopping. Guests can enjoy amenities such as free Wi-Fi, complimentary breakfast, and a fitness center. With its friendly staff and affordable rates, Red Roof Inn & Suites Chestertown is the perfect choice for a relaxing stay in this picturesque town.

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.

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.

The Driftwood Inn is a charming lodging establishment located at 609 Washington Avenue in the picturesque town of Chestertown, Maryland. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to relax and unwind. With its convenient location near the waterfront and local attractions, the Driftwood Inn is the perfect home base for exploring all that Chestertown has to offer. Whether you're visiting for business or pleasure, the Driftwood Inn provides a convenient and comfortable stay 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.

Welcome to the historic Chestertown bed and breakfast, the Inn at Mitchell House. Rated among the top ten out of 10,000 by "America's Historic Inns," this charming 18th-century manor home is situated on 12 manicured acres between Chestertown and Rock Hall, Maryland. Just a half mile away from the Chesapeake Bay, guests can enjoy the private beach and full services of the Tolchester Marina. Operating year-round, seven days a week, the inn offers six guestrooms, two parlors, a dining room, a screened porch, and numerous fireplaces creating a casual and friendly atmosphere. All rooms and the cottage include modern amenities such as a TV, hairdryer, iron, wireless internet, and use of the 2nd-floor refrigerator. Rates include a full country breakfast for two guests per room.

Located in Chestertown, Maryland, the Brampton Bed and Breakfast Inn offers comfortable and luxurious accommodations on 35 acres of landscaped gardens, meadows, and forest. With thirteen unique accommodations, including rooms in the manor house and private cottages, each room is carefully appointed with private en-suite bathrooms, luxury linens, smart TVs, and fast wireless internet. Enjoy a romantic retreat with amenities such as wood-burning fireplaces and modern ensuite bathrooms. The historic Brampton Inn, built in 1860 and listed on the National Registry of Historic Places, is a short distance from the quaint town of Chestertown and Washington College. Experience gourmet dining on the beautiful Renaissance Garden terrace or indulge in curated experiences such as a couples' float spa session or a private vineyard tour with wine tasting.

The John L Stam House is a charming lodging and tourist attraction located at 114 Washington Avenue in Chestertown, Maryland, United States. This historic building offers guests a unique and cozy place to stay while exploring the beautiful town of Chestertown. With its picturesque surroundings and convenient location, the John L Stam House is the perfect destination for travelers looking to experience the rich history and culture of Maryland's Eastern Shore.