TOP 30 Hotel in Chestertown, Maryland

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Chestertown Cove Apartments is a luxurious residential community located at 408 Morgnec Road in Chestertown, Maryland. Our apartments offer modern amenities and spacious floor plans, perfect for those seeking a comfortable and convenient living experience. Residents can enjoy beautiful views of the cove and easy access to nearby shopping, dining, and entertainment options. With a friendly and professional management team on-site, Chestertown Cove Apartments is the ideal place to call home in the charming town of Chestertown.

Chestertown Landing Apartments is a waterfront community situated at 100 Schooner Way in Chestertown, Maryland. Our luxurious apartments offer stunning views of the Chester River and are conveniently located near shopping, dining, and entertainment options. Residents can enjoy a variety of amenities including a swimming pool, fitness center, and community clubhouse. With spacious floor plans, modern finishes, and a prime location, Chestertown Landing Apartments provides the perfect blend of comfort and convenience for residents looking for upscale living in a picturesque setting.

Chestertown Landing II is a premier waterfront apartment complex located at 200 Clipper Way in Chestertown, Maryland, United States. Nestled along the scenic Chester River, this community offers luxurious living with stunning views and convenient access to outdoor recreation. Residents can enjoy spacious and modern apartments, top-notch amenities such as a fitness center, swimming pool, and clubhouse, as well as a prime location near shopping, dining, and entertainment options. Experience waterfront living at its finest at Chestertown Landing II.

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.

Duck Neck Campground is a serene retreat nestled in the heart of Chestertown, Maryland. Located at 500 Double Creek Point Road, this picturesque campground offers a perfect blend of nature and comfort for visitors seeking a peaceful getaway. With a variety of lodging options including cabins, RV sites, and tent camping, guests can enjoy the beauty of the surrounding park while still having all the amenities they need. Whether you're looking to relax by the campfire, explore the nearby hiking trails, or simply unwind in nature, Duck Neck Campground is the ideal destination for outdoor enthusiasts of all ages.

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.

Calvert Heights is a prestigious institution located at 103 Hawkins Drive in Chestertown, Maryland, United States. Known for its academic excellence and strong sense of community, Calvert Heights offers a wide range of programs and resources to support student success. With a dedicated faculty and staff, state-of-the-art facilities, and a vibrant campus atmosphere, Calvert Heights is committed to providing a top-tier education and preparing students for future success. Whether you're interested in STEM fields, the arts, or humanities, Calvert Heights has something for everyone. Come visit us today and see why Calvert Heights is the perfect place to pursue your academic goals.

Kent Crossing and Colonial Manor Apartments offer luxurious living just outside of downtown Chestertown, Maryland. Located at 101 Morgnec Road, these properties boast inspired floor plans and high-quality construction. Residents will enjoy being in close proximity to all the amenities and attractions that downtown Chestertown has to offer. Whether you're looking for a one-bedroom apartment or a spacious two-bedroom unit, Kent Crossing and Colonial Manor have the perfect home for you. Experience the best of Chestertown living at these beautiful apartment communities.

Happy Run Kennel is a premier dog boarding and training facility located at 301 Hoffecker Road in Chestertown, Maryland. Our experienced staff provides top-notch care and attention to all of our furry guests, ensuring they have a safe and comfortable stay while their owners are away. We offer spacious indoor and outdoor play areas, cozy sleeping quarters, and personalized training programs to meet the individual needs of each dog. At Happy Run Kennel, we strive to create a fun and welcoming environment for dogs of all sizes and breeds. Visit us today and see why we are the go-to destination for pet owners in Chestertown and beyond.

JBK Hardware is your one-stop shop for all your hardware and home goods needs in Chestertown, Maryland. From tools and building supplies to kitchenware and home decor, we have everything you need to complete your next project or spruce up your living space. Our friendly and knowledgeable staff are always on hand to assist you with finding the perfect products for your needs. Visit us at our convenient location in Chestertown to experience top-notch customer service and quality products at affordable prices.

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.

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.

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.

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.

Hill's Inn is a charming lodging establishment located at 114 Washington Avenue in the historic town of Chestertown, Maryland. Our inn offers cozy and comfortable accommodations for guests looking to experience the beauty and charm of the Eastern Shore. Each room is tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Guests can relax in our inviting common areas or explore the nearby shops, restaurants, and attractions. Whether you're visiting for business or pleasure, Hill's Inn provides a welcoming and convenient home away from home.

The White Swan Tavern is a charming historic inn located at 231 High Street in Chestertown, Maryland. This cozy lodging establishment offers a unique and memorable stay for guests visiting the United States. With its quaint atmosphere and convenient location, the White Swan Tavern provides a comfortable and welcoming experience for travelers looking to explore the beautiful town of Chestertown. Whether you are visiting for business or pleasure, the White Swan Tavern is the perfect place to relax and unwind during your stay in Maryland.

Fairlee Corporation is a reputable real estate agency located at 23165 Baywood Court in Chestertown, Maryland. With years of experience in the industry, our dedicated team of professionals is committed to providing top-notch services to clients looking to buy, sell, or rent properties in the area. Whether you are a first-time homebuyer or a seasoned investor, Fairlee Corporation is here to help you navigate the competitive real estate market and make informed decisions. Contact us today to learn more about our comprehensive services and personalized approach to real estate.

Brookmeadow Apartments is a charming residential community located at 150 Flatland Road in Chestertown, Maryland, United States. Nestled in a peaceful and picturesque setting, Brookmeadow Apartments offers a variety of spacious and well-appointed apartment homes for individuals and families alike. Residents can enjoy modern amenities such as a swimming pool, fitness center, and beautifully landscaped grounds. With a convenient location near shopping, dining, and entertainment options, Brookmeadow Apartments provides a comfortable and convenient living experience for all.

P W Property Management Inc is a reputable property management company located at 202 Philosophers Terrace in Chestertown, Maryland. With years of experience in the industry, we specialize in managing residential and commercial properties to ensure they are well-maintained and profitable for our clients. Our dedicated team of professionals provides top-notch customer service and works diligently to meet the unique needs of each property owner. Whether you are looking for assistance with leasing, maintenance, or financial management, P W Property Management Inc is here to help. Trust us to take care of your property investment and maximize its potential. Contact us today to learn more about our services.

Upper Shore Aging Housing Corporation is a health institution located at 402 Morgnec Road in Chestertown, Maryland, United States. This facility is dedicated to providing housing and support services for aging individuals in the Upper Shore region. With a focus on promoting independence and well-being, the corporation offers a range of amenities and programs tailored to meet the unique needs of older adults. Whether it's assistance with daily tasks, access to medical care, or simply a sense of community, Upper Shore Aging Housing Corporation strives to enhance the quality of life for seniors in the area.

Kent Attainable Housing, Inc. is a non-profit organization based in Chestertown, Maryland, United States. Our mission is to provide affordable housing solutions for individuals and families in need within the Kent County community. Located at 114 South Lynchburg Street, our dedicated team works tirelessly to ensure that everyone has access to safe and stable housing options. Whether you are looking to rent or purchase a home, Kent Attainable Housing, Inc. is here to help you achieve your housing goals. Contact us today to learn more about our programs and services.

Select Land & Homes Inc is a reputable real estate agency located at 97 South Queen Street in the charming town of Chestertown, Maryland, United States. Our team of experienced professionals is dedicated to helping clients find their dream homes or investment properties in the area. Whether you are looking to buy, sell, or rent, we are here to provide top-notch service and guidance every step of the way. Trust Select Land & Homes Inc for all your real estate needs in Chestertown and beyond.

Coldwell Banker Chesapeake Real Estate Company, located at 114 South Cross Street in Chestertown, Maryland, is a top-rated real estate agency serving the Eastern Shore of Maryland, Delaware, and Chester County, PA since 2010. With offices strategically located in Easton, Chestertown, and Chesapeake City, our team of professional agents and brokers are dedicated to helping you navigate the complex process of buying or selling properties with professionalism, sincerity, and integrity. At Coldwell Banker Chesapeake Real Estate, you will find a wide selection of Eastern Shore houses, waterfront homes, land properties, and farm properties for sale. Our team offers expert advice on market conditions, the best marketing strategies, and personalized services to ensure a stress-free experience for our clients.

Robert L Davis Real Estate is a trusted real estate agency located at 852 Washington Avenue in Chestertown, Maryland. With a team of experienced and knowledgeable agents, we are dedicated to helping our clients buy, sell, and rent properties in the area. Whether you are looking for your dream home or trying to find the perfect investment opportunity, our team is here to guide you through the entire process. Contact us today to start your real estate journey with Robert L Davis Real Estate.

Cross Street Realtors is a reputable real estate agency located at 201 South Cross Street in Chestertown, Maryland. With a team of experienced and knowledgeable real estate professionals, we are dedicated to helping our clients buy, sell, or rent properties in the area. Whether you are looking for a new home, investment property, or commercial space, our agents are here to assist you every step of the way. Trust Cross Street Realtors to provide excellent service and guidance in all your real estate needs.

Jennifer Connor, Realtor, and The Revel Home Team of Coldwell Banker Realty are dedicated to providing top-notch real estate services in Chestertown, Maryland. Located at 114 South Cross Street, their team of experienced professionals is committed to helping clients find their dream homes or sell their properties with ease. With a focus on personalized service and attention to detail, Jennifer Connor and her team strive to make the buying or selling process as smooth and stress-free as possible. Whether you are looking to buy a new home or sell your current property, trust Jennifer Connor and The Revel Home Team to help you achieve your real estate goals.