A boat docked at a pier during twilight with a city skyline in the background.

Chester 5 Stars Hotels

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Check availability on Chester 5 Star Hotels

Tonight
Sep 2 - Sep 3
Tomorrow
Sep 3 - Sep 4
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Chester 5-star hotels

Room
Golf
Suite, 1 Bedroom (Water View)
Room

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Andrew
NT$19,095
NT$21,004 total
includes taxes & fees
Sep 7 - Sep 8
Inn at Perry Cabin
Pool
Front of property
Interior
Taylor's Suite

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
United States
James
NT$12,555
NT$14,312 total
includes taxes & fees
Sep 24 - Sep 25
The Inn at Tacaro Estate
Restaurant
The Asian Suite
Interior
Exterior

3. Inn at 202 Dover

Inn at 202 Dover
Easton
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
NT$2,625
NT$2,993 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (1,151 reviews)
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

126 West St Annapolis MD
NT$4,847
NT$5,525 total
Sep 8 - Sep 9
includes taxes & fees
Graduate by Hilton Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD
NT$6,812
NT$7,765 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (990 reviews)
Annapolis Waterfront Hotel, Autograph Collection
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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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A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr

Top Chester Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"All staff were very pleasant, engaged, and helpful. Everyone seems to genuinely care about making the experience memorable. The property, setting, grounds, and amenities are beautiful and well-maintained."
John 1-night trip
Posted 1 day ago
Inn at Perry Cabin

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$2,993
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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