Chestertown 5 Stars Hotels

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Check availability on Chestertown 5 Star Hotels

Tonight
Feb 3 - Feb 4
Tomorrow
Feb 4 - Feb 5
This weekend
Feb 6 - Feb 8
Next weekend
Feb 13 - Feb 15

Our top choices for Chestertown 5-star hotels

Fells Point Suite | Premium bedding, down comforters, pillowtop beds, minibar

Pendry Baltimore

Pendry Baltimore
5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1,000 reviews)
"My favorite baltimore hotel hands down!"
United States
Dontay
The price is NT$10,619
NT$13,778 total
includes taxes & fees
Feb 17 - Feb 18
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$6,404 per night from Feb 15 to Feb 16
NT$6,404
NT$7,301 total
Feb 15 - Feb 16
includes taxes & fees
8.8/10 Excellent! (901 reviews)
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PoolSpaHot tubBreakfast includedWaterpark
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
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"My favorite baltimore hotel hands down!"
Dontay 1-night trip
Posted 5 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$6,275

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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