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

5 Stars Hotels in Chestertown, Maryland from CA $298

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Check availability on Chestertown 5 Star Hotels

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Chestertown 5-star hotels

Exterior

1. Pendry Baltimore

Pendry Baltimore
5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1,000 reviews)
"A gorgeous property in the best location with the nicest staff."
United States
Zachary
The price is CA $581
CA $741 total
includes taxes & fees
Aug 16 - Aug 17
Pendry Baltimore
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chestertown.
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD
The price is CA $261 per night from Aug 9 to Aug 10
CA $261
CA $298 total
Aug 9 - Aug 10
includes taxes & fees
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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.

Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"A gorgeous property in the best location with the nicest staff."
Zachary 3-night trip
Posted 4 days ago
Pendry Baltimore

Find out more about Chestertown

Five Star Hotels in Chestertown

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Chestertown so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Chestertown and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Chestertown

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Chestertown

The results are in, and Chestertown 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Chestertown! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Chestertown today and settle down in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chestertown?
How much you pay for a 5-star hotel in Chestertown depends on things like when you want to go and the length of your stay. A top tip for landing the best deal? Use our pricing filters to compare all of the available options for your selected dates.

  • Search for the lowest price per night from CA $298

What makes a hotel 5 stars in Chestertown?
Exemplary guest service is the hallmark of every 5-star hotel in Chestertown. From the instant you arrive, staff are at your beck and call, whether arranging customized tours or providing a turn-down service. In addition, hotels have to feature top-rate conveniences to be entitled to a 5-star rating. These can include deluxe baths, a wellness centre, pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chestertown?
Find a luxury escape that includes your lodging, meals, drinks and entertainment in Chestertown with our filters. Search for properties rated 5 stars and click on the "All inclusive" filter. Make sure you check what's included in the upfront price. This way, you can take full advantage of the many perks on offer from the moment you step into the lobby.

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