Photo by Patricia Knorr

Find 4 Star Hotels in Chester, MD from $121

Start date: Check-in selected.
To Date
End date: Check-out

    Upfront pricing

    Our total price for your stay includes taxes and fees

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

    Be picky

    Search almost a million properties worldwide

Check availability on Chester 4 Star Hotels

Compare Chester 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

View from property
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1011)
"Staff was outstanding!"
$155 nightly
The price is $177
Nov 10 - Nov 11
Total with taxes and fees
Graduate by Hilton Annapolis
Garden
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1018)
"Comfortable place to stay, nice shopping area close by. "
$106 nightly
The price is $121
Oct 19 - Oct 20
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
View from property
The Westin Annapolis
The Westin Annapolis
4.0 star property
8.6 out of 10, Excellent, (1006)
"Would stay there again very soon "
$179 nightly
The price is $204
Oct 26 - Oct 27
Total with taxes and fees
The Westin Annapolis
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
8.8 out of 10, Excellent, (871)
"Clean room. Friendly staff awesome location. "
$203 nightly
The price is $232
Nov 9 - Nov 10
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (422)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
$217 nightly
The price is $241
Nov 9 - Nov 10
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
Front of property
The Oaks Waterfront
The Oaks Waterfront
4.0 star property
10.0 out of 10, Exceptional, (38)
"Loved the Oaks! Fabulous accommodations and excellent staff"
$459 nightly
The price is $505
Oct 19 - Oct 20
Total with taxes and fees
The Oaks Waterfront
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
$400 nightly
The price is $440 total per night from Nov 17 to Nov 18
$440 total
Nov 17 - Nov 18
Total with taxes and fees
9.4/10 Exceptional! (365 reviews)
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
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Staff was outstanding!"
Fred 2-night trip
Posted 4 days ago
Graduate by Hilton 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 $440

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.

Explore a world of travel with Expedia