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Find 5 Star Hotels in Chestertown, MD from SAR 769

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Check availability on Chestertown 5 Star Hotels

Tonight
26 Jul - 27 Jul
Tomorrow
27 Jul - 28 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

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

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

Sagamore Pendry Baltimore

5.0 star property
9.4 out of 10, Exceptional, (1007)
"Great place for staycation."
The price is SAR 1,276
SAR 1,653 total
includes taxes & fees
19 Aug - 20 Aug
Sagamore 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 826 per night from Aug 17 to Aug 18
SAR 826
SAR 942 total
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (843 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

Quaint Chestertown awaits: its sports, university life, art, and more!

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Somewhere over the rainbow... Terrific view on the plane back to the North.
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Top Chestertown Hotel Reviews

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

10/10 Excellent
"BEST QUICK GET AWAY EVER !!!!! GREAT SERVICE, AND VERY FRIENDLY"
Craig 2-night trip
Posted 5 days ago
Sagamore 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 769

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.