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

Compare and book 5 Star hotels in Chester, Maryland

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Check availability on Chester 5 Star Hotels

This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Chester 5-star hotels

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

1. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (395 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is 16.321.122 ₫
17.953.234 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, pool loungers

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (18 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is 8.949.284 ₫
10.202.147 ₫ total
includes taxes & fees
11 Aug - 12 Aug
The Inn at Tacaro Estate
Dinner served

3. 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 2.658.424 ₫ per night from 30 Aug to 31 Aug
2.658.424 ₫
3.030.604 ₫ total
30 Aug - 31 Aug
includes taxes & fees
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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
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?
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 3.030.604 ₫

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.