Photo by Patricia Knorr

Find 5 Star Hotels in Chester, MD from AED 368

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Check availability on Chester 5 Star Hotels

Tonight
4 Aug - 5 Aug
Tomorrow
5 Aug - 6 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

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

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

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (356)
"Beautiful place to stay."
The price is AED 2,165
AED 2,620 total
includes taxes & fees
1 Sep - 2 Sep
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)
"1940’s estate is maintained to remind you of those times. There was a “Speak-EZ” in the basement they had open Friday and Saturday evenings. My room was spacious and included a balcony. Huge front lawn with a pool and a view to the Bay. "
The price is AED 1,134
AED 1,293 total
includes taxes & fees
10 Aug - 11 Aug
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.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court, Annapolis, MD
The price is AED 368 per night from Aug 10 to Aug 11
AED 368
AED 420 total
10 Aug - 11 Aug
includes taxes & fees
8.4/10 Very Good! (1,008 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

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Staff were wonderful, beautiful property and the restaurant was great. We enjoyed the complementary 5pm champagne toast and historical stories."
Joseph 1-night trip
Posted 3 days ago
Inn at Perry Cabin

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 AED 368

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.