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Chestertown 5 Stars Hotels

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Check availability on Chestertown 5 Star Hotels

Tonight
Aug 8 - Aug 9
Tomorrow
Aug 9 - Aug 10
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

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

Sagamore Pendry Baltimore
Enjoy waterfront views from this property's central pool, situated on a man-made dock with access to the water.

Sagamore Pendry Baltimore

5.0 star property
9.4 out of 10, Exceptional, (1004)
"Beautiful, professional establishment. "
The price is NT$10,239
NT$13,255 total
includes taxes & fees
Aug 24 - Aug 25
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 NT$7,059 per night from Aug 17 to Aug 18
NT$7,059
NT$8,047 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (850 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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Open Photo by Assya A

Top Chestertown Hotel Reviews

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

10/10 Excellent
"Everything was top notch. You don’t find this service and attention to detail anymore, "
Emily 3-night trip
Posted 21 hours ago
Sagamore 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$6,102

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.