Find 5 Star Hotels in Chestertown, MD from SAR 626

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Check availability on Chestertown 5 Star Hotels

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Compare Chestertown 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

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

Pendry Baltimore

5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1004)
"Great hotel"
United States
kimberly
The price is SAR 1,185
SAR 1,547 total
includes taxes & fees
25 Dec - 26 Dec
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 SAR 549 per night from Dec 18 to Dec 19
SAR 549
SAR 626 total
18 Dec - 19 Dec
includes taxes & fees
8.8/10 Excellent! (876 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.

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
"Clean room, valet services, front desk, restaurant bar service"
Detra 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?
How much you pay for a 5-star hotel in Chestertown depends on factors like when you plan to go and the length of your stay. An insider tip for bagging the best deal? Use our pricing filters to check out all of the available hotels for your preferred dates.

  • Search for the lowest price per night from SAR 626

What makes a hotel 5 stars in Chestertown?
In Chestertown, a hotel must offer a certain number of upscale amenities to be rated 5 stars. These can include on-site gyms, gourmet restaurants, saunas and spas, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their outstanding service. You'll enjoy things like in-room massages, nightly turn-down services and concierge services. Some may also offer special touches like welcome gifts.
Are there any 5-star all-inclusive resorts in Chestertown?
Our filters are the best way to narrow down what you're looking for. Select "5-star" and "All inclusive" to see the most luxurious properties in Chestertown where your meals, lodging, entertainment and activities are included in the price. At these escapes, your trip is pure leisure from the moment you put down your suitcase.

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