Photo by Assya A

Search Luxury Hotels in Chestertown

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Luxury Hotels

Tonight
21 Jul - 22 Jul
Tomorrow
22 Jul - 23 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Top Chestertown Luxury Hotels

Driftwood Inn
Rows of rooms with stone facades and windows line the building's side.

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
Quiana
The price is ₹5,471
₹6,073 total
includes taxes & fees
26 Jul - 27 Jul
Driftwood Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Stayed at the Historic Inns of Annapolis - Governor Calvert House. The front desk receptionist was friendly and helpful. Check in was easy and efficient. Valet parked the car and due to being centrally located, we didn't use the car for the two days we were in Annapolis. The room was clean and the bed was comfortable. Very quiet. We would definitely stay here again! "
Mary 2-night trip
Posted 4 days ago
Historic Inns of Annapolis

Frequently asked questions

Are you searching for the perfect hotel for your luxury trip to Chestertown?
Use Expedia to help you arrange a flight to Baltimore, MD (MTN-Martin State) airport or Easton, MD (ESN-Easton - Newnam) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chestertown offers. During your visit, you might want to enjoy the university which Chestertown is known for.
How many luxury hotels will I be able to find in Chestertown?
Lie in the lap of luxury during your getaway to Chestertown in one of Expedia's 6 luxury hotels.
When can I expect good weather in Chestertown?
Planning for the weather is an important factor for making your trip to Chestertown a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What's there to see and do in Chestertown?
When you're in Chestertown, enjoy exploring the sights and attractions here including Historical Society of Kent County Maryland, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater. If you have extra time while you're in the area, you might want to see Chestertown Historic District and Sumner Hall.