Explore top 2026 4 Star Hotels in Chestertown

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Top Chestertown 4 Star hotels

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

Fully refundableReserve now, pay when you stay

$237 nightly

$270 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD

Fully refundableReserve now, pay when you stay

$214 nightly

$238 total

Oct 19 - Oct 20

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this traditional hotel. Enjoy the seasonal outdoor pool and perks like free self parking ...

Hudson house

3037 Hudson St Baltimore MD

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage, laundry facilities, and barbecue grills are also ...

7.6/10 Good! (5 reviews)

"Tried messaging multiple times prior to check in to confirm check in process and possibility of checking in early, no response. Finally called upon arrival, was told they had to confirm my reservation and would call back, after waiting an hour, called 3x no answer, eventually spoke to someone else ..."

Reviewed on Sep 3, 2026

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Rooftop Patio w/ View: Baltimore Retreat

Baltimore MD

This apartment includes free WiFi in public areas and barbecue grills.

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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.

4 Star Hotels Chestertown

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Chestertown 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Chestertown will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Chestertown, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.