Find Luxury Hotels in Chestertown, MD

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Check availability on Chestertown Luxury Hotels

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, (436 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is NT$4,922
NT$6,266 total
includes taxes & fees
Feb 16 - Feb 17
The Inn at Chesapeake Bay Beach Club
Premium bedding, down comforters, pillowtop 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, (901 reviews)
"Great location, nice and clean "
United States
Micah
The price is NT$6,411
NT$7,309 total
includes taxes & fees
Feb 25 - Feb 26
Annapolis Waterfront Hotel, Autograph Collection
Exterior

Pendry Baltimore

Pendry Baltimore
5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1,000 reviews)
"My favorite baltimore hotel hands down!"
United States
Dontay
The price is NT$11,993
NT$15,390 total
includes taxes & fees
Mar 12 - Mar 13
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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10/10 Excellent
"Rooms were great, but they were FREEZING. had the heater on all night and didn’t help at all. other than that the room was great!"
Sarah 1-night trip
Posted 6 days ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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 Northern Chesapeake Bay, Chesapeake Bay, and Historical Society of Kent County Maryland. If you have extra time while you're in the area, you might want to see Garfield Center for the Arts at the Prince Theater and Chestertown Historic District.

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