Chestertown, Maryland Hotels and Accommodation

Chestertown

Visit Chestertown’s directory of accommodations or view local accommodations on TripAdvisor.

Kent County

Check out Kent County B&B and Inn listings made available through the Kent County Lodging Association. 

Comfort Inn & Suites

Pet-friendly hotel offers free parking, free WiFi throughout and a free hot breakfast each morning. Also available to guests are a fitness center, on-site laundry facilities, friendly 24-hour reception, and a business center featuring a print station.

Click here to view their website.

Red Roof Inn & Suites

Offers free WiFi, a guest coin laundry facility and free coffee in the lobby. Guests also have access to designated pet area and free parking. Red Roof Inn & Suites Chestertown is a pet-friendly hotel where two well-behaved pets per room are welcome.

Click here to view their website.

Great Oak Manor

Great Oak Manor, one of Maryland’s newest luxury boutique hotels, is a 12-room Manor, with a Carriage House, situated on 15.2 private acres with an oasis of stately trees with a Grand Lawn, private beach and ever-changing picturesque views of Chesapeake Bay located eight miles from historic Chestertown, MD.  Newly owned as of 2022, the manor has recently undergone a full renovation, completed in May 2024. Great Oak Manor focuses on exemplary hospitality, modern & luxurious conveniences, and shared experiences and is a gracious property to host family gatherings, couples or group friends’ getaways, small meetings, reunions, celebrations from milestone birthdays and anniversaries to graduations, or intimate/micro-weddings. Great Oak Manor is an adults-only property welcoming guests 18 years or older.

Click here to view their website.

VRBO

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Disclaimer: We do not endorse VRBO rentals and cannot answer for property management issues.

AirBnB

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Disclaimer: We do not endorse the AirBnB and cannot answer for property management issues.