The Best Free parking 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.

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.

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.

Hot Diggity Dawg Pet Services, located at 7515 Poplar Avenue in Chestertown, Maryland, offers a range of services for your furry friends. From Doggy Daycare and boarding to dog walking, trips to the dog park, and transportation to vet and grooming appointments, we have everything your pet needs. Our safe, open-play environment is completely cage and kennel free, allowing your dog to enjoy playtime in a secure 5.5-foot privacy fenced area. All dogs must be at least 16 weeks old and up to date on vaccinations to participate in our services. Doggy Daycare runs Monday-Saturday from 8am-5pm, with full day drop-ins available for $10.00 per additional dog. We also offer transportation to and from daycare for an extra fee.