Vacation rentals 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.

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.

Joelle Dolch Cross Street Realtors is a prestigious real estate agency located at 201 South Cross Street in Chestertown, Maryland, United States. With a team of experienced and dedicated professionals, we specialize in helping clients buy, sell, and rent properties in the Chestertown area. Our commitment to personalized service and attention to detail sets us apart in the competitive real estate market. Whether you are looking for your dream home, investment property, or commercial space, Joelle Dolch Cross Street Realtors is here to help you every step of the way. Contact us today to learn more about our services and how we can assist you with your real estate needs.

Terri Kulp - Coldwell Banker Chesapeake Real Estate is a premier real estate institution located at 114B South Cross Street in Chestertown, Maryland. Specializing in waterfront properties, vacation homes, military relocations, and first-time homebuyers, Terri Kulp offers personalized assistance to help you find your dream home in this charming region along the Chesapeake Bay. With offices strategically located in Easton, Chestertown, and Chesapeake City, Coldwell Banker Chesapeake Real Estate provides unparalleled services to guide you through the process of buying or selling a home in the Eastern Shore of Maryland, Delaware, and Chester County, PA. Whether you are looking to upsize, downsize, or find your waterfront luxury dream home, Terri Kulp and her team are dedicated to helping you make informed decisions on your real estate journey. Contact Coldwell Banker Chesapeake Real Estate today to begin your search for the perfect home in this picturesque part of the country.

Village House is a one-stop destination for all your home furnishing and renovation needs. Located at 103 South Cross Street in Chestertown, Maryland, this institution offers a wide range of furniture, home goods, and contracting services. Whether you're looking to spruce up your living room with a new sofa, remodel your kitchen with custom cabinets, or simply find that perfect accent piece for your home, Village House has you covered. With a team of experienced professionals and a diverse selection of high-quality products, Village House is the go-to store for all your home improvement projects.

Cliff Point Retreat is a luxurious getaway nestled in the serene surroundings of Chestertown, Maryland. As a real estate and travel agency, we specialize in providing our clients with the ultimate vacation experience. Our stunning property at 4670 Cliffs City Road offers breathtaking views of the cliffs and the city, creating the perfect backdrop for a relaxing and rejuvenating escape. Whether you're looking to invest in a new property or searching for the perfect vacation rental, Cliff Point Retreat has everything you need to make your dreams a reality. Come visit us and experience the beauty and tranquility of Cliff Point Retreat.

Victory Farm is a charming institution located at 24420 Chestertown Road in Chestertown, Maryland. This unique establishment offers a combination of food and lodging, providing guests with a peaceful and serene retreat in the heart of the countryside. The farm is known for its fresh and delicious farm-to-table meals, made with locally sourced ingredients. Guests can also enjoy comfortable and cozy accommodations, perfect for a relaxing getaway. Whether you're looking to escape the hustle and bustle of city life or simply want to experience the beauty of rural Maryland, Victory Farm is the perfect destination for a memorable stay.

Enterprise Rent-A-Car is a trusted car rental institution located at 121 Flatland Road in Chestertown, Maryland, United States. With a wide range of vehicles to choose from, including economy cars, SUVs, and trucks, Enterprise offers convenient and reliable transportation solutions for both business and leisure travelers. Their friendly and knowledgeable staff are dedicated to providing exceptional customer service, making the rental process smooth and hassle-free. Whether you need a vehicle for a day trip or an extended vacation, Enterprise Rent-A-Car is the go-to choice for all your rental needs.

Cruise Business is a luxury travel agency located at 209 North Queen Street in Chestertown, Maryland, United States. Partnering with prestigious companies like Four Seasons Yachts, Marc-Henry Cruise Holdings Ltd, and Fincantieri, Cruise Business offers unparalleled luxury cruises and yacht experiences. The agency provides exclusive access to some of the world's most stunning destinations, including China, the Bahamas, and Grand Bahama. With a focus on sustainability, Cruise Business also collaborates with shipbuilders like Meyer Werft and Chantiers de l'Atlantique to ensure environmentally friendly cruise options. Whether you're looking for a relaxing island getaway or an adventurous exploration of iconic cities, Cruise Business has a cruise itinerary to suit your every desire. Experience the ultimate in luxury and comfort at sea with Cruise Business.

Kent County Visitors Info is a local government office and travel agency located at 122 North Cross Street in Chestertown, Maryland, United States. Our knowledgeable staff is dedicated to providing visitors with information about the many attractions, events, and activities in Kent County. Whether you're looking for recommendations on where to stay, dine, or explore, we are here to help make your visit to our charming county a memorable experience. Stop by our office or give us a call to start planning your trip today!

Brittland Estates is a multi-faceted institution located at 205 Cannon Street in Chestertown, Maryland. As a health facility, we offer a range of services to promote wellness and vitality. Additionally, we operate as a real estate agency, helping clients find their dream homes in the beautiful Chestertown area. Our travel agency services cater to those looking to explore new destinations and create unforgettable experiences. With a commitment to excellence and customer satisfaction, Brittland Estates is your one-stop destination for all your health, real estate, and travel needs.

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.

The Lodge at Great Oak Landing is a charming lodging facility located at 22170 Great Oak Landing Road in Chestertown, Maryland, United States. Nestled in a picturesque setting, this institution offers guests a peaceful retreat with stunning views of the surrounding natural beauty. The Lodge provides comfortable accommodations, excellent amenities, and exceptional service to ensure a memorable stay for visitors. Whether you are looking for a relaxing getaway or a fun-filled vacation, The Lodge at Great Oak Landing is the perfect choice for your next adventure.

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.