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Find 5 Star Hotels in Chester, MD from $130

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Check availability on Chester 5 Star Hotels

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Sep 2 - Sep 3
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Sep 5 - Sep 7
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Sep 12 - Sep 14

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

Our top choices for Chester 5-star hotels

Inn at Perry Cabin
Breakfast, lunch, dinner served; ocean views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (361)
"Beautiful place to stay."
$619 nightly
The price is $681
Sep 4 - Sep 5
Total with taxes and fees
Inn at Perry Cabin
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"It was perfect!! We had a great stay. Luca was so kind and attentive. The property is astonishing. Perfect weekend retreat! Thank you so much "
$306 nightly
The price is $349
Sep 7 - Sep 8
Total with taxes and fees
The Inn at Tacaro Estate
Inn at 202 Dover
Dinner served

Inn at 202 Dover

5.0 star property
10.0 out of 10, Exceptional, (14)
"Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience."
Inn at 202 Dover
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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.
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

126 West St, Annapolis, MD
$180 nightly
The price is $205 total per night from Sep 21 to Sep 22
$205 total
Sep 21 - Sep 22
Total with taxes and fees
9.2/10 Wonderful! (973 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 Chester

Chester awaits: its island views, sunny weather, golf, and more!

See all hotels in Chester
Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Find out more about Chester

Find out more about Chester

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 $130

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.