Photo by Patricia Knorr

Chester 5 Stars Hotels

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Our top choices for Chester 5-star hotels

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

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is NT$16,462
NT$19,919 total
includes taxes & fees
Dec 23 - Dec 24
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, sun loungers
The Inn at Tacaro Estate

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (11)
"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

Inn at 202 Dover
5.0 star property
Easton
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."
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 NT$2,354 per night from Jan 4 to Jan 5
NT$2,354
NT$2,683 total
Jan 4 - 2026/1/5
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

Top Chester Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chester?
You can find several pricing options for a 5-star hotel in Chester on Expedia. The amount you pay will depend on when you want to travel, length of stay and other factors. Compare all of the available properties for your desired dates and use our pricing and other filters to find the perfect luxury stay.

  • Search for the lowest price per night from NT$2,683

What makes a hotel 5 stars in Chester?
From high-end restaurants and all-day gyms to pools and dreamy bedding, the 5-star experience in Chester is all about indulgence and comfort. But it takes more than just upscale amenities to get a 5-star rating. Hotels must also offer extraordinary guest-focused services like massage treatments, dry cleaning and laundry and room service any time night or day.
Are there any 5-star all-inclusive resorts in Chester?
Find a luxury retreat that includes your lodging, meals, drinks and entertainment in Chester with the help of Expedia's filter tool. Search for properties rated 5 stars and select the "All inclusive" filter. Have a look at what's included in the purchase price. That way, you're ready to take advantage of the premium perks on offer as soon as you arrive.

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