4 Stars Hotels in Chester, Maryland from CA $179

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Check availability on Chester 4 Star Hotels

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, (1,004 reviews)
"The staff was great, nice hotel bar and the location was close to everything!"
United States
Diane
The price is CA $157
CA $179 total
includes taxes & fees
Jul 5 - Jul 6
DoubleTree by Hilton Hotel Annapolis
View from property

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.2 out of 10, Wonderful, (1,000 reviews)
"Very fine place"
United States
David
The price is CA $231
CA $263 total
includes taxes & fees
Jul 12 - Jul 13
Graduate by Hilton Annapolis
Lobby lounge

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,002 reviews)
"Good location, nice hotel"
United States
Jiyoung
The price is CA $253
CA $289 total
includes taxes & fees
Jul 12 - Jul 13
The Westin 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, (938 reviews)
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
United States
Salvatore
The price is CA $360
CA $410 total
includes taxes & fees
Jul 20 - Jul 21
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
Stevensville
9.4 out of 10, Exceptional, (463 reviews)
"Wonderful stay! Everything was amazing..,the staff, rooms, Knoxie’s Table, the spa! Couldn’t have asked for a better stay. I’ll definitely return."
United States
Damika
The price is CA $319
CA $390 total
includes taxes & fees
Jul 6 - Jul 7
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, (42 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is CA $622
CA $684 total
includes taxes & fees
Jun 22 - Jun 23
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 $1,011 per night from Jun 22 to Jun 23
CA $1,011
CA $1,113 total
Jun 22 - Jun 23
includes taxes & fees
9.6/10 Exceptional! (390 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!

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Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"We had a girls trip for two nights and it was perfect. Quiet but beautiful, the pool was so nice and relaxing. Great food. Good spot. Would come back again!"
Michelle 2-night trip
Posted 6 hours ago
The Inn at Chesapeake Bay Beach Club

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 $541

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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