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

Find 5 Star Hotels in Chestertown, MD from AED 862

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Check availability on Chestertown 5 Star Hotels

Next weekend
31 Jul - 2 Aug
In two weeks
7 Aug - 9 Aug

Our top choices for Chestertown 5-star hotels

Exterior

Pendry Baltimore

Pendry Baltimore
5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1,001 reviews)
"Beautiful space and wonderful staff"
United States
Camille
The price is AED 1,488
AED 1,899 total
includes taxes & fees
27 Jul - 28 Jul
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 AED 756 per night from Aug 5 to Aug 6
AED 756
AED 862 total
5 Aug - 6 Aug
includes taxes & fees
8.8/10 Excellent! (949 reviews)
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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 harbor.

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
"Wonderful experience at this Pendry location."
Elizabeth 1-night trip
Posted 2 days ago
Pendry Baltimore

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 factors like when you plan to go and the length of your stay. An insider tip for bagging the best deal? Use our pricing filters to check out all of the available hotels for your preferred dates.

  • Search for the lowest price per night from AED 862

What makes a hotel 5 stars in Chestertown?
In Chestertown, a hotel must offer a certain number of upscale amenities to be rated 5 stars. These can include on-site gyms, gourmet restaurants, saunas and spas, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their outstanding service. You'll enjoy things like in-room massages, nightly turn-down services and concierge services. Some may also offer special touches like welcome gifts.
Are there any 5-star all-inclusive resorts in Chestertown?
Our filters are the best way to narrow down what you're looking for. Select "5-star" and "All inclusive" to see the most luxurious properties in Chestertown where your meals, lodging, entertainment and activities are included in the price. At these escapes, your trip is pure leisure from the moment you put down your suitcase.