Photo by Patricia Knorr

Chester Hotel Guide - 4 Stars Hotels in Chester, Maryland

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Check availability on Chester 4 Star Hotels

Top Chester 4 Star Hotels

DoubleTree by Hilton Hotel Annapolis
Welcome to DoubleTree by Hilton, featuring a traditional brick facade and a distinctive peaked roof.

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1006)
"Excellent hospitable staff made the stay even better!"
The price is Rp1.666.782
Rp1.900.132 total
includes taxes & fees
17 Aug - 18 Aug
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis
Enjoy serene sailing and stunning views of the marina, surrounded by historic landmarks.

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1000)
"Great stay! Would come here again."
The price is Rp2.532.528
Rp2.887.082 total
includes taxes & fees
3 Aug - 4 Aug
Graduate by Hilton Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Relax in this serene room with a large bed, a comfortable armchair, and a floor lamp, offering a view of the nearby water.

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (839)
"Front desk staff was very friendly and helpful."
The price is Rp3.585.583
Rp4.087.565 total
includes taxes & fees
24 Jul - 25 Jul
Annapolis Waterfront Hotel, Autograph Collection
The Westin Annapolis
Experience the grandeur of this classic hotel, featuring a symmetrical facade with a central entrance and evenly spaced windows.

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1001)
"Easy downtown location, walkable to waterfront and great restaurants "
The price is Rp2.598.219
Rp2.961.970 total
includes taxes & fees
10 Aug - 11 Aug
The Westin Annapolis
The Inn at Chesapeake Bay Beach Club
Welcome to our hotel, featuring a modern entrance with a covered area and lush greenery.

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (401)
"Staff was very polite and friendly. "
The price is Rp3.513.315
Rp4.315.495 total
includes taxes & fees
22 Jul - 23 Jul
The Inn at Chesapeake Bay Beach Club
The Oaks Waterfront
Stately home with a central entrance and two wings, set amidst manicured lawns and shaded by trees.

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (32)
" Beautiful property, wonderful staff, excellent food service."
The price is Rp6.728.160
Rp7.400.976 total
includes taxes & fees
20 Jul - 21 Jul
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 Rp10.368.364 per night from 29 Jul to 30 Jul
Rp10.368.364
Rp12.545.803 total
29 Jul - 30 Jul
includes taxes & fees
9.4/10 Exceptional! (355 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.

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Photo by Patricia Knorr
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Top Chester Hotel Reviews

Frequently asked questions

What are the best 4-star hotels in Chester?
Expedia customers give top marks to The Inn at Chesapeake Bay Beach Club. From its handy amenities to its attentive staff, every aspect of this 4-star hotel in Chester is designed to deliver an incredible holiday experience.
How much does it cost to stay in a 4-star hotel in Chester?
To find a 4-star hotel in Chester that fits your budget, use Expedia's handy search filters. Take a look at the available options during your holiday dates and use our pricing filter to set your limit. You can also sort your results by the most wallet-friendly escape first.

  • Search for the lowest price from Rp10.368.364

What's the difference between 5-star and 4-star hotels in Chester?
If you choose to holiday at a 4-star hotel in Chester, you'll usually find plenty of amenities to keep you relaxed, such as a gym, restaurant and pool. You can enjoy top-quality service and upmarket accommodation. Opt for a 5-star hotel and you'll have access to a few extra perks — think on-site spas, 24-hour front desk and nightly turndown services. You're likely to get more amenities and first-class services at a 5-star retreat, though both are fabulous options for luxury guests.