An aerial view of a town with a river, buildings, and surrounding greenery.

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Check availability on Chestertown Luxury Hotels

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Chestertown luxury hotels

A historic building with a prominent facade, large arched windows, and a central entrance.
A modern outdoor seating area with a built-in fireplace, two grey sofas, and a round table with drinks.
A modern lounge area with round tables, cushioned chairs, and a large floral painting on the wall.
A waterfront hotel with a pool, outdoor seating, and a view of the cityscape.

1. Pendry Baltimore

Pendry Baltimore
Fells Point
  • Immerse in harbor-side luxury at Baltimore's Pendry hotel, where elegant relaxation meets waterfront sophistication.
₹38,350
₹48,966 total
includes taxes & fees
20 Nov - 21 Nov
Pendry Baltimore
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

2. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
₹20,298
₹24,946 total
includes taxes & fees
15 Nov - 16 Nov
The Inn at Chesapeake Bay Beach Club
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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great accommodation. Would definitely stay here again. Great location."
Wayne And Karen 1-night trip
Posted less than an hour 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.
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, Chestertown Historic District and Rolphs Wharf Marina. If you have extra time while you're in the area, you might want to see Northern Chesapeake Bay and Chesapeake Bay.

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