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Chestertown Hotel Guide - 5 Stars Hotels in Chestertown, Maryland

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Check availability on Chestertown 5 Star Hotels

Tonight
25 Jun - 26 Jun
Tomorrow
26 Jun - 27 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Top Chestertown 5 Star Hotels

Sagamore Pendry Baltimore
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas

Sagamore Pendry Baltimore

5.0 star property
9.4 out of 10, Exceptional, (1003)
"Great place for staycation."
The price is Rp5.625.776
Rp7.282.927 total
includes taxes & fees
21 Jul - 22 Jul
Sagamore 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 Rp3.799.530 per night from 27 Jul to 28 Jul
Rp3.799.530
Rp4.331.465 total
27 Jul - 28 Jul
includes taxes & fees
8.8/10 Excellent! (829 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.

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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 Rp3.516.110

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.