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

Find 4 Star Hotels in Chester, MD from $110

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Check availability on Chester 4 Star Hotels

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Oct 4 - Oct 5
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Oct 5 - Oct 6
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Oct 9 - Oct 11
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Oct 16 - Oct 18

Our top choices for Chester 4-star hotels

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.
A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.
A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

1. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Michele
$97 nightly
$110 total
Oct 12 - Oct 13
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.
A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.
A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.
A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

2. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Humberto
$147 nightly
$167 total
Oct 26 - Oct 27
Total with taxes and fees
Graduate by Hilton Annapolis
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.
A store with shelves of beverages, a counter with a cash register, and baskets with items.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

3. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Bobbi
$199 nightly
$227 total
Oct 5 - Oct 6
Total with taxes and fees
The Westin Annapolis
A balcony with a table set for two, overlooking a marina with boats.
A hotel room with a large bed, a chair, a small table, and a view of a body of water.
A waterfront area with boats docked, a clear sky, and buildings in the background.
The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

4. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
William
$231 nightly
$264 total
Nov 1 - Nov 2
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
$214 nightly
$238 total
Oct 19 - Oct 20
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

6. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
$489 nightly
$538 total
Oct 5 - Oct 6
Total with taxes and fees
The Oaks Waterfront
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chester.
Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
$570 nightly
$627 total
Oct 26 - Oct 27
Total with taxes and fees
9.6/10 Exceptional! (405 reviews)
Inn at Perry Cabin
The Inn at Tacaro Estate

The Inn at Tacaro Estate

6220 Town Point Rd Tracys Landing MD
$366 nightly
$417 total
Oct 7 - Oct 8
Total with taxes and fees
9.6/10 Exceptional! (19 reviews)
The Inn at Tacaro Estate
Inn at 202 Dover

Inn at 202 Dover

202 East Dover Street Easton MD
Get ratesInn at 202 Dover
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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
A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr

Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great Hotel in a very central location"
Mark 2-night trip
Posted 15 hours ago
Graduate by Hilton Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 13 days ago
The Westin Annapolis

Find out more about Chester

Chester Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Chester, Maryland are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Chester 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Chester. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Chester, Maryland, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Chester hotels offer everything your heart desires.

Frequently asked questions

What are the best 4-star hotels in Chester?
Expedia customers highly rate The Inn at Chesapeake Bay Beach Club. From its handy amenities to its welcoming staff, everything about this 4-star hotel in Chester is designed to provide an exceptional vacation experience.
How much does it cost to stay in a 4-star hotel in Chester?
With Expedia's filter tool, scoring an awesome deal on a 4-star hotel in Chester just got simpler. Start by entering your chosen arrival date and length of your escape. Then list the results by price and pick a property that best matches your budget and style.
  • Search for the lowest price from $417
What's the difference between 5-star and 4-star hotels in Chester?
Offering an inviting traveler experience and upmarket décor, 4-star hotels are a fabulous option for your Chester getaway. These kinds of stays generally feature lots of handy amenities that make it easy to kick back and relax — think complimentary bathrobes, restaurants and pools. Or get a taste of the high life at a 5-star hotel designed to pamper with luxury perks and amenities. Round-the-clock concierge service, premium toiletries and world-class dining are typically included at these deluxe retreats.

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