Chester Hotel Guide - 5 Stars Hotels in Chester, Maryland

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Check availability on Chester 5 Star Hotels

Tonight
5 Mar - 6 Mar
Tomorrow
6 Mar - 7 Mar
This weekend
6 Mar - 8 Mar
Next weekend
13 Mar - 15 Mar

Our top choices for Chester 5-star hotels

Premium bedding, down duvets, in-room safe, desk

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (374 reviews)
"Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay. "
United States
Joseph
The price is Rp6.251.076
Rp6.876.184 total
includes taxes & fees
8 Mar - 9 Mar
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, pool loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
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 reviews)
"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 Rp1.508.019 per night from 15 Mar to 16 Mar
Rp1.508.019
Rp1.719.142 total
15 Mar - 16 Mar
includes taxes & fees
8.6/10 Excellent! (1,011 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

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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 Rp1.719.142

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.