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

Jul 1 - Jul 2

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 ...

8.8/10 Excellent! (936 reviews)

"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"

Reviewed on Jun 5, 2026

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD

Fully refundableReserve now, pay when you stay

$249 nightly

$276 total

Jun 15 - Jun 16

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 ...

9.4/10 Exceptional! (457 reviews)

"The hotel was clean and the staff were really nice. More of a resort than a hotel. I would recommend for the perfect getaway."

Reviewed on Jun 7, 2026

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 ...

10/10 Exceptional! (2 reviews)

"I loved being in canton as the square is a few minute walk. I love Baltimore and i will definitely rent the Hudson house upon my return. Everything is within a short distance of you need groceries or restaurants. I lived in Baltimore for eight years and this house is definitely in an ideal ..."

Reviewed on Apr 17, 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.

Recent Chestertown hotel reviews by fellow wanderers

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5

Posted 3 hours ago

Travelocity Verified Review

"No one told me that the elevator was down prior to me booking the reservations. Traveling up and down the stairs was very exhausting."

A verified traveler stayed at La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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

5 out of 5

Posted 4 hours ago

Travelocity Verified Review

"The room had plenty of space and the room was very clean. Plenty of parking available in th front and the breakfast had a pretty good selection. A couple of the items had to be heated up but a microwave is available."

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

Historic Inns of Annapolis

2 out of 5

Posted 1 day ago

Travelocity Verified Review

"The property is in a great location. Plenty to do in the area without having to drive. Unfortunately the staff are less than helpful. We checked out at 11am. At 12 noon, we realized we left a bag hanging from the bathroom door. Called, staff said they wou look into it. Took down my number and address. Called them back a few hours later and they claim no one turned in a bag. Hello, the cleaning staff was going in this room before the next guest at 4pm and the receptionist could have called the cleaning staff to grab it for us. Nope, I guess the receptionist job description doesn't include taking any initiative."

A verified traveler stayed at Historic Inns of Annapolis

The Lodge at Great Oak Landing

2 out of 5

Posted 1 day ago

Travelocity Verified Review

"We left 1 hour after arrival... Enough said! This is very much a buyer beware situation. It's no resort. There was absolutely no food available. Tiki bar is permanently closed. Small restaurant was also closed and our only option was food from the front desk. It's about a 30 minute drive to the closest restaurant. The response from the front desk was simply "most restaurants around here are closed on Mondays and Tuesdays." That doesn't help a stranded traveler at your hotel. How does a resort not have any food available? HUGE red flag. The beach is hundreds of yards from the hotel with in and out access only available to hotel guests during office hours of 8:00 to 4:30. This is very much a marina first and a hotel second if not fifth. The staff was nonchalant & unwelcoming. The best decision we made truly was leaving."

A verified traveler stayed at The Lodge at Great Oak Landing