4 Stars Hotels in Chester, Maryland from CA $138

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Check availability on Chester 4 Star Hotels

Tonight
Mar 7 - Mar 8
Tomorrow
Mar 8 - Mar 9
Next weekend
Mar 13 - Mar 15
In two weeks
Mar 20 - Mar 22

Our top choices for Chester 4-star hotels

Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,014 reviews)
"The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. "
United States
Kathy
The price is CA $121
CA $138 total
includes taxes & fees
Mar 15 - Mar 16
DoubleTree by Hilton Hotel Annapolis
Lobby

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,002 reviews)
"Room was clean, great location"
United States
Brian
The price is CA $228
CA $260 total
includes taxes & fees
Mar 22 - Mar 23
Graduate by Hilton Annapolis
Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (906 reviews)
"Great location, nice and clean "
United States
Micah
The price is CA $287
CA $327 total
includes taxes & fees
Mar 29 - Mar 30
Annapolis Waterfront Hotel, Autograph Collection
Property amenity

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,002 reviews)
"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
The price is CA $243
CA $277 total
includes taxes & fees
Mar 8 - Mar 9
The Westin Annapolis
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (439 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is CA $225
CA $284 total
includes taxes & fees
Mar 9 - Mar 10
The Inn at Chesapeake Bay Beach Club
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is CA $597
CA $657 total
includes taxes & fees
Mar 8 - Mar 9
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
The price is CA $503 per night from Mar 24 to Mar 25
CA $503
CA $553 total
Mar 24 - Mar 25
includes taxes & fees
9.6/10 Exceptional! (374 reviews)
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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
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"I stayed here as I did a visit for my youngest son who is attending Bowie. While I stayed most of the time on campus, I found when I was at the hotel I found the staff and facility both inviting, warm and cordial. "
Kent Andrew 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Chester

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chester are calling your name. Known for providing first-rate service in amazing locations, each of the Chester 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Chester. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chester, Maryland, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chester hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

What are the best 4-star hotels in Chester?
Relax in comfort at The Inn at Chesapeake Bay Beach Club. According to reviews by travellers, this is one of Chester's favourite 4-star hotels.
How much does it cost to stay in a 4-star hotel in Chester?
We can help you quickly find the perfect 4-star hotel for your stay in Chester. Use our filter tool to fine-tune your search by things like amenities, budget and property star rating and get access to fabulous deals in a few clicks.

  • Search for the lowest price from CA $553

What's the difference between 5-star and 4-star hotels in Chester?
If you decide to spend your vacation at a 4-star hotel in Chester, you'll typically find loads of amenities to keep you relaxed, such as a gym, pool and restaurant. You can enjoy excellent service and deluxe accommodations. Pick a 5-star hotel and you'll get a few extra perks — think concierge assistance, on-site spas and opulent turndown services. You'll most likely get extra amenities and premium services at a 5-star getaway, but both are great options for luxury guests.

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