Find 5 Star Hotels in Chestertown, MD from SAR 993

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Check availability on Chestertown 5 Star Hotels

Tonight
2 May - 3 May
Tomorrow
3 May - 4 May
Next weekend
8 May - 10 May
In two weeks
15 May - 17 May

Our top choices for Chestertown 5-star hotels

Exterior

Pendry Baltimore

Pendry Baltimore
5.0 star property
Fells Point
9.4 out of 10, Exceptional, (1,001 reviews)
"Fantastic hotel all the way around! "
United States
ALISHA
The price is SAR 1,365
SAR 1,758 total
includes taxes & fees
31 May - 1 Jun
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 934 per night from May 3 to May 4
SAR 934
SAR 1,065 total
3 May - 4 May
includes taxes & fees
8.8/10 Excellent! (924 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

4/10 Poor
"Stayed at Pendry Baltimore recently and was disappointed. The cleanliness was poor; bathroom ceiling had cracked paint and the ventilation system appeared moldy. Service at the bar was also lacking, with staff coming off as rude and inattentive. Food quality didn’t help either; the meatballs were extremely salty. For the price point, this property should feel premium and well maintained. Having visited a few years ago, I can clearly notice a decline in overall standards."
giancarlo 3-night trip
Posted 2 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 993

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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