Are there any 5-star vacation rentals in Chester?

Our site doesn't offer any 5-star vacation rentals in Chester. However, you can still find a range of top-rated stays where the only thing on your itinerary will be to kick back and have fun. View what's available by searching through our vacation rentals in Chester .

The Best 5 Star Hotels in Chester, MD from SAR 325

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.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Chester 5 Star Hotels

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Chester 5-star hotels

Breakfast, lunch, dinner served; ocean views

Inn at Perry Cabin

Downtown St. Michaels

Ellen

SAR 1,968 total

includes taxes & fees

27 Feb - 28 Feb

Seasonal outdoor pool, pool umbrellas, sun loungers

The Inn at Tacaro Estate

Tracys Landing

Todd

Inn at 202 Dover

Easton

James

Save an average of 15% on thousands of hotels when you're signed in

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 285

SAR 325 total

8 Feb - 9 Feb

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Still don't see what you're looking for?

See all properties in Chester.

You can also use these popular filters to refine your search.

Pool Spa Hot tub Breakfast included Waterpark

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

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 325

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.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Chester 5 Star Hotels