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Find 5 Star Hotels in Chester, MD from $118

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

Exterior
Inn at 202 Dover
5.0 star property
9.8 out of 10, Exceptional, (14)
"We stayed in the French Room at the Inn at 202Dover in Easton, MD. We were welcomed by the manager, Vincent. The room was just as beautiful as it looked in the photos! The whole inn is a gem! The only thing I didn't end up trying was the hydrojet massage bathtub. There were directions in the guest book in the room but it just seemed too complicated for me. We also didn't use the steam shower, just had regular showers. We had dinner on the Friday night at the Inn and the food was delicious...
Inn at 202 Dover
Breakfast, lunch, dinner served; ocean views
Inn at Perry Cabin
5.0 star property
9.6 out of 10, Exceptional, (296)
"Mason and Michael at the front desk were extremely helpful."
The price is $665
$805 total
includes taxes & fees
May 23 - May 24
Inn at Perry Cabin

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 Annapolis

Graduate Annapolis

126 West St, Annapolis, MD
The price is $212 per night from Jun 2 to Jun 3
$212
$242 total
includes taxes & fees
Jun 2 - Jun 3
9.2/10 Wonderful! (1,054 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.

Chester Five Star Hotel Information

If you’re searching for the celebrity treatment, the 5 star hotels in Chester are your dreams come true. From sprawling resorts to fancy hot spots, theseChester 5 star hotels immerse each traveler in the most elite experience money can buy. Want to unwind with a VIP-worthy spa treatment? These hotels have the leisure you're looking for.

Interested in sampling world-class cuisine? The on-site restaurants at the 5 stars hotels in Chester, Maryland, let you do just that. You’ll even be able to book a room (or perhaps a penthouse?) at first-rate hotels near the region’s can’t-miss sights and most bustling shopping centers. Plus, many globe-trotters who visit Chester five star hotels find incredible rates and deep discounts thanks to Expedia, so you can score a deal without sacrificing an ounce of quality.

Everything you could possibly want (and a few things you didn’t know you needed): That’s what you’ll receive when you stay at Chester 5 star hotels.

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 $118

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.
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.