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

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Check availability on Chestertown Luxury Hotels

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

Our top choices for Chestertown luxury hotels

Front of property – evening/night

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, (467 reviews)
The price is ₹21,298
₹26,042 total
includes taxes & fees
30 Jun - 1 Jul
The Inn at Chesapeake Bay Beach Club
Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (939 reviews)
The price is ₹23,506
₹26,797 total
includes taxes & fees
5 Jul - 6 Jul
Annapolis Waterfront Hotel, Autograph Collection
Exterior

Pendry Baltimore

Pendry Baltimore
5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Immerse in harbor-side luxury at Baltimore's Pendry hotel, where elegant relaxation meets waterfront sophistication.
The price is ₹30,209
₹39,378 total
includes taxes & fees
13 Jul - 14 Jul
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.
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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"The Johnson House was very well maintained, was welcoming with a historic flair. The access to downtown was easy, and felt very safe."
Cassady 4-night trip
Posted 6 hours 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 Chestertown Historic District, 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 Historical Society of Kent County Maryland.

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