Chestertown Hotel Guide - 5 Stars Hotels in Chestertown, Maryland

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Check availability on Chestertown 5 Star Hotels

Tonight
26 Jan - 27 Jan
Tomorrow
27 Jan - 28 Jan
This weekend
30 Jan - 1 Feb
Next weekend
6 Feb - 8 Feb

Our top choices for Chestertown 5-star hotels

Sagamore Suite | Premium bedding, down duvets, pillow-top beds, minibar

Pendry Baltimore

Pendry Baltimore
5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1,002 reviews)
"The hotel was beautiful, and the staff was courteous and friendly. "
United States
Amy
The price is Rp5.853.360
Rp7.569.504 total
includes taxes & fees
17 Feb - 18 Feb
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 Rp3.131.043 per night from 15 Feb to 16 Feb
Rp3.131.043
Rp3.569.390 total
15 Feb - 16 Feb
includes taxes & fees
8.8/10 Excellent! (899 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 harbour.

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Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

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 can vary based on what time of year you travel and how long you plan to be away, among other factors. Use our price per night filter and other search tools to score the best deal on a plush stay.

  • Search for the lowest price per night from Rp3.339.611

What makes a hotel 5 stars in Chestertown?
Flawless guest service is the hallmark of every 5-star hotel in Chestertown. From the moment you arrive, staff ensure your every need is met, whether recommending activities and tours or providing a turn-down service. Plus, hotels have to offer superior amenities to obtain a 5-star rating. These can include luxury bathrooms, a wellness centre, pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chestertown?
Use our filter tool to find an upmarket escape in Chestertown where most of what you need is included in the price. After your initial search, narrow down your results for resorts that have a rating of 5 stars and are described as "All inclusive." The main thing on the agenda at these stays? Relaxation and enjoyment.