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Compare and book 5 Star hotels in Chester, Maryland

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Check availability on Chester 5 Star Hotels

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sep - 7 Sep

Top Chester 5 Star Hotels

Our top choices for Chester 5-star hotels

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

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (361)
"Beautiful place to stay."
The price is 15.062.454 ₫
18.225.701 ₫ total
includes taxes & fees
17 Sept - 18 Sept
Inn at Perry Cabin
The Inn at Tacaro Estate
Horse riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"Amazing hospitality "
The price is 9.145.796 ₫
10.426.170 ₫ total
includes taxes & fees
7 Sept - 8 Sept
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
The price is 4.680.453 ₫ per night from 2 Sept to 3 Sept
4.680.453 ₫
5.335.716 ₫ total
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (1,003 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!

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Photo by Patricia Knorr
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Top Chester Hotel Reviews

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chester?
The amount you pay for a 5-star hotel in Chester can vary based on what time of year you travel and how long you plan to be away, among several factors. Take advantage of our price per night filter and other search tools to land the best deal on a luxurious getaway.

  • Search for the lowest price per night from 3.004.057 ₫

What makes a hotel 5 stars in Chester?
Outstanding guest service characterises every 5-star hotel in Chester. From the moment you arrive, staff cater to your every whim, whether offering luggage assistance and storage or providing in-room massage treatments. In addition, hotels must feature superior conveniences to meet the standard for a 5-star rating. These can include luxury bathrooms, saunas or spas, swimming pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chester?
Use our filter tool to find a luxury escape in Chester where most of what you need is included in the price. From there, refine your results for accommodation that have a 5-star rating and are deemed "All inclusive." The most important thing on the agenda at these stays? Relaxation and enjoyment.