Photo by Patricia Knorr

Find 5 Star Hotels in Chester, MD from SAR 259

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Check availability on Chester 5 Star Hotels

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

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

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

Inn at Perry Cabin

5.0 star property
St. Michaels
9.6 out of 10, Exceptional, (370)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is SAR 1,361
SAR 1,647 total
includes taxes & fees
4 Dec - 5 Dec
Inn at Perry Cabin
Horseback riding
The Inn at Tacaro Estate

The Inn at Tacaro Estate

5.0 star property
Tracys Landing
9.2 out of 10, Wonderful, (10)
"Amazing, warm, gracious setting. Can’t wait to return "
United States
Andrea
The Inn at Tacaro Estate
Dinner served
Inn at 202 Dover

Inn at 202 Dover

5.0 star property
Easton
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."
United States
James
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 SAR 227 per night from Dec 21 to Dec 22
SAR 227
SAR 259 total
21 Dec - 22 Dec
includes taxes & fees
8.6/10 Excellent! (1,027 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

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 SAR 259

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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