Chestertown, Maryland Hotels and Accommodation

Chestertown and the surrounding areas offer some charming B&Bs and Inns in addition to two national hotel chains just a few blocks from campus.

Accommodations

Chestertown and Kent County, MD

Kent County

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

Hotel Options

Comfort Inn & Suites Chestertown Exterior

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.

A photo of the Red Roof Inn & Suites in Chestertown, Maryland

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.

A photo of Great Oak Manor

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.

Disclaimer: Washington College does not endorse any hotels and cannot answer for experiences with hotel staff or cleanliness.

Rental Options

vrbo rental home in chestertown

VRBO

Click here to view their website.

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

airbnb rental in chestertown

AirBnB

Click here to view their website.

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

Not finding anything you like?

Search for more hotels in the area