Compare and book 5 Star hotels in Chester, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester 5 Star Hotels

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul

Our top choices for Chester 5-star hotels

Breakfast, lunch, dinner and brunch served

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (390 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is 18.806.843 ₫
20.687.528 ₫ total
includes taxes & fees
9 Jul - 10 Jul
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
9.6 out of 10, Exceptional, (16 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is 8.961.542 ₫
10.216.121 ₫ total
includes taxes & fees
20 Jul - 21 Jul
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 2.926.562 ₫ per night from 5 Jul to 6 Jul
2.926.562 ₫
3.336.281 ₫ total
5 Jul - 6 Jul
includes taxes & fees
Still don't see what you're looking for?
See all properties in Chester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It was a wonderful stay. The rooms were clean, the staff helpful and the food marvelous. I intend to visit again!"
Bill 2-night trip
Posted 12 days ago
Inn at Perry Cabin

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 3.336.281 ₫

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.