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Chestertown 5 Stars Hotels

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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.

Pendry Baltimore
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas
Pendry Baltimore
5.0 star property
9.4 out of 10, Exceptional, (1004)
"Great hotel"
The price is NT$10,887
NT$14,050 total
includes taxes & fees
Nov 6 - Nov 7
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$6,213 per night from Nov 9 to Nov 10
NT$6,213
NT$7,083 total
Nov 9 - Nov 10
includes taxes & fees
8.8/10 Excellent! (871 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
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
"Love this hotel! Absolutely beautiful - from the pool on the harbor, to the atrium, to the restaurant - it's truly outstanding. The staff is also incredibly accomodating. I forgot several articles of clothing and they mailed them to me immediately. I highly recommend the Sagamore Pendry!"
Christine 2-night trip
Posted 9 days 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$7,083

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.

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