Find 5 Star Hotels in Chester, MD from SAR 418
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14 Aug - 15 AugTomorrow
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14 Aug - 16 AugNext weekend
21 Aug - 23 AugOur top choices for Chester 5-star hotels
SAR 2,500
SAR 2,750 total
includes taxes & fees
1 Sep - 2 Sep
SAR 1,375
SAR 1,567 total
includes taxes & fees
23 Aug - 24 Aug
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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
SAR 366
SAR 418 total
30 Aug - 31 Aug
includes taxes & fees
Graduate by Hilton Annapolis
126 West St Annapolis MD
SAR 525
SAR 599 total
23 Aug - 24 Aug
includes taxes & fees
9.4/10 Exceptional! (1,017 reviews)
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
SAR 778
SAR 887 total
23 Aug - 24 Aug
includes taxes & fees
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Chester awaits: its island views, sunny weather, golf, and more!
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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.
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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.