Compare and book 5 Star hotels in Chestertown, Maryland
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7 Aug - 8 AugTomorrow
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14 Aug - 16 AugOur top choices for Chestertown 5-star hotels
9.014.520 ₫
11.669.872 ₫ total
includes taxes & fees
7 Sept - 8 Sept
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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
80 Compromise St Annapolis MD
5.429.676 ₫
6.189.831 ₫ total
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (964 reviews)
The Inn at Chesapeake Bay Beach Club
180 Pier One Road Stevensville MD
5.660.727 ₫
6.951.207 ₫ total
31 Aug - 1 Sept
includes taxes & fees
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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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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 6.189.831 ₫
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.