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

Chestertown 5 Stars Hotels

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Check availability on Chestertown 5 Star Hotels

Tonight
Sep 5 - Sep 6
Tomorrow
Sep 6 - Sep 7
Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20

Our top choices for Chestertown 5-star hotels

Exterior
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas
Interior
Interior

1. Pendry Baltimore

Pendry Baltimore
Fells Point
United States
Russell
NT$10,884
NT$14,090 total
includes taxes & fees
Sep 28 - Sep 29
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
NT$6,809
NT$7,762 total
Oct 4 - Oct 5
includes taxes & fees
Annapolis Waterfront Hotel, Autograph Collection
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD
NT$6,051
NT$7,522 total
Sep 8 - Sep 9
includes taxes & fees
The Inn at Chesapeake Bay Beach Club
Hudson house

Hudson house

3037 Hudson St Baltimore MD
Get rates
7.6/10 Good! (5 reviews)
Hudson house
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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.

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chestertown?
There are a range of pricing options for a 5-star hotel in Chestertown on Expedia. The amount you pay will depend on your travel dates, trip length and other factors. Compare all of the available accommodations for your desired dates and use our pricing and other filters to score the perfect luxury stay.
  • Search for the lowest price per night from NT$7,522
What makes a hotel 5 stars in Chestertown?
In Chestertown, a hotel needs to provide a specific number of high-end amenities to earn 5 stars. These may include gourmet restaurants, on-site gyms, saunas and spas, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their superior service. You'll enjoy things like in-room massages, concierge services and nightly turn-down services. Some may also offer additional touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Chestertown?
Our handy filters are the easiest way to search for exactly what you want. Select "All inclusive" and "5-star" to see the most upscale properties in Chestertown where your meals, accommodations, activities and entertainment are included in the upfront price. At these getaways, your trip is absolute indulgence from the moment you arrive.

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