Find 5 Star Hotels in Chester, MD from $111
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Aug 30 - Aug 31Next weekend
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Sep 11 - Sep 13Our top choices for Chester 5-star hotels
$504 nightly
$554 total
Sep 23 - Sep 24
Total with taxes and fees
$441 nightly
$502 total
Aug 30 - Aug 31
Total with taxes and fees
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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 Chester.
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$98 nightly
$111 total
Sep 27 - Sep 28
Total with taxes and fees
8.8/10 Excellent! (1,134 reviews)
Graduate by Hilton Annapolis
126 West St Annapolis MD
$153 nightly
$175 total
Sep 13 - Sep 14
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
$215 nightly
$245 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (982 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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Chester awaits: its island views, sunny weather, golf, and more!
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Chester Five Star Hotel Information
If you’re searching for the celebrity treatment, the 5 star hotels in Chester are your dreams come true. From sprawling resorts to fancy hot spots, theseChester 5 star hotels immerse each traveler in the most elite experience money can buy. Want to unwind with a VIP-worthy spa treatment? These hotels have the leisure you're looking for.
Interested in sampling world-class cuisine? The on-site restaurants at the 5 stars hotels in Chester, Maryland, let you do just that. You’ll even be able to book a room (or perhaps a penthouse?) at first-rate hotels near the region’s can’t-miss sights and most bustling shopping centers. Plus, many globe-trotters who visit Chester five star hotels find incredible rates and deep discounts thanks to Expedia, so you can score a deal without sacrificing an ounce of quality.
Everything you could possibly want (and a few things you didn’t know you needed): That’s what you’ll receive when you stay at Chester 5 star hotels.
Frequently asked questions
How much does it cost to stay in a 5-star hotel in Chester?
How much you pay for a 5-star hotel in Chester can vary based on when you prefer to travel and how long you plan to stay, among other factors. Take advantage of our price per night filter and other search tools to land the best rate on a plush stay.
- Search for the lowest price per night from $111
What makes a hotel 5 stars in Chester?
From fine dining venues and 24/7 fitness centers to pools and the finest bedding, the 5-star experience in Chester is all about comfort and luxury. But it requires more than just upscale amenities to receive a 5-star rating. Accommodations must also deliver extraordinary guest-centric services like in-room massages, on-site dry cleaning and laundry and 24-hour concierge services.
Are there any 5-star all-inclusive resorts in Chester?
Use Expedia's filter tool to find a luxury escape in Chester where everything you need is included. After your initial search, refine your results for accommodations that have a 5-star rating and are described as "All inclusive." The first thing on the itinerary at these stays? Pure enjoyment and indulgence.
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