Chestertown Hotel Guide - 5 Stars Hotels in Chestertown, Maryland

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Check availability on Chestertown 5 Star Hotels

Tonight
30 Apr - 1 May
Tomorrow
1 May - 2 May
This weekend
1 May - 3 May
Next weekend
8 May - 10 May

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, (1,000 reviews)
"Fantastic hotel all the way around! "
United States
ALISHA
The price is Rp5.613.624
Rp7.308.625 total
includes taxes & fees
27 May - 28 May
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 Rp4.350.559 per night from 25 May to 26 May
Rp4.350.559
Rp4.959.638 total
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (924 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.

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

Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"NA"
Andrea 2-night trip
Posted 11 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 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 Rp4.588.062

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.