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Find 5 Star Hotels in Chestertown, MD from SAR 671

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Check availability on Chestertown 5 Star Hotels

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

Sagamore Pendry Baltimore
Lobby

Sagamore Pendry Baltimore

5.0 star property
9.4 out of 10, Exceptional, (1000)
"We stayed at the Sagamore in Baltimore, and overall, it was a great experience. Check-in was quick, and our room was beautiful. However, we encountered a slight issue—the heat wasn’t working on Valentine’s Day, which was disappointing. The next day, Saturday, we brought it to the front desk’s attention, and they promptly upgraded us to a larger stateroom. From that point on, our stay was excellent. We truly appreciated how quickly they accommodated us and the great service we received."
The price is SAR 1,230
SAR 1,600 total
includes taxes & fees
13 Apr - 14 Apr
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 773 per night from Mar 31 to Apr 1
SAR 773
SAR 881 total
includes taxes & fees
31 Mar - 1 Apr
8.8/10 Excellent! (803 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.

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Somewhere over the rainbow... Terrific view on the plane back to the North.
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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 671

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.
Are there any 5-star vacation rentals in Chestertown?
You won’t find any 5-star vacation rentals in Chestertown on our site, but there are a range of other highly rated options worth checking out. Scan through our vacation rentals in Chestertown to book the best place for your getaway.