Find Luxury Hotels in Chestertown, MD

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Our top choices for Chestertown luxury hotels

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (443 reviews)
"Very clean room, staff was very nice. "
United States
Byron
The price is NT$5,954
NT$7,425 total
includes taxes & fees
Apr 5 - Apr 6
The Inn at Chesapeake Bay Beach Club

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (914 reviews)
"Great waterfront room with roomy balcony. Gym was nice also. Can't wait for the var and restaurants to open."
United States
Douglas
The price is NT$8,622
NT$9,829 total
includes taxes & fees
Apr 12 - Apr 13
Annapolis Waterfront Hotel, Autograph Collection

Pendry Baltimore

Pendry Baltimore
5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1,000 reviews)
"Great hotel!"
United States
James
The price is NT$11,378
NT$14,688 total
includes taxes & fees
Apr 5 - Apr 6
Pendry Baltimore
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

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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
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 Northern Chesapeake Bay. If you have extra time while you're in the area, you might want to see Chesapeake Bay and Garfield Center for the Arts at the Prince Theater.

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