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Chestertown 5 Stars Hotels

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Our top choices for Chestertown 5-star hotels

Exterior
Pendry Baltimore

Pendry Baltimore

Pendry Baltimore
5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1001)
"Really nice cozy room we had the terrace balcony would definitely stay again!"
United States
Takema
The price is NT$10,731
NT$13,892 total
includes taxes & fees
Jan 4 - 2026/1/5
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 NT$5,542 per night from Dec 22 to Dec 23
NT$5,542
NT$6,317 total
Dec 22 - Dec 23
includes taxes & fees
8.8/10 Excellent! (881 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 harbor.

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

Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Really nice cozy room we had the terrace balcony would definitely stay again!"
Takema 1-night trip
Posted 6 days ago
Pendry Baltimore

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$6,317

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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