A coastal town with a marina, a bridge, and a highway.

4 Stars Hotels in Chester, Maryland from CA $144

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Check availability on Chester 4 Star Hotels

Our top choices for Chester 4-star hotels

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.

1. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.2 out of 10, Wonderful, (1,013 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is CA $184
CA $210 total
includes taxes & fees
Nov 29 - Nov 30
Graduate by Hilton Annapolis
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

2. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,275 reviews)
"Excellent staff & service!"
United States
Michele
The price is CA $126
CA $144 total
includes taxes & fees
Nov 23 - Nov 24
DoubleTree by Hilton Hotel Annapolis
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

3. 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, (514 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is CA $256
CA $320 total
includes taxes & fees
Dec 9 - Dec 10
The Inn at Chesapeake Bay Beach Club
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

4. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,005 reviews)
"Excellent location, Very nice Hotel"
United States
Loraine
The price is CA $232
CA $264 total
includes taxes & fees
Nov 15 - Nov 16
The Westin Annapolis
A balcony with a table set for two, overlooking a marina with boats.

5. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
United States
Donna
The price is CA $304
CA $346 total
includes taxes & fees
Nov 23 - Nov 24
Annapolis Waterfront Hotel, Autograph Collection
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

6. The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (46 reviews)
"Absolutely perfect little 3 day get away. The entire atmosphere was excellent, great complementary breakfast from menu, beautiful modern rooms, perfectly manicured landscaping with lots of seating for relaxing by the water. The entire staff were so friendly and helpful. We made an excellent choice and would definitely go back. 10+ out of 10."
United States
William
The price is CA $621
CA $684 total
includes taxes & fees
Nov 12 - Nov 13
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 $615 per night from Dec 9 to Dec 10
CA $615
CA $676 total
Dec 9 - Dec 10
includes taxes & fees
9.6/10 Exceptional! (407 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
A coastal town with a marina, a bridge, and a highway.

Top Chester Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"The perfect getaway weekend with my husband! Will definitely go back."
Carolina 2-night trip
Posted 1 day 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 $479

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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