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

Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1002)
"Great area and it was a perfect hotel for our trip. "
The price is Rp2.597.550
Rp2.961.207 total
includes taxes & fees
2 Sept - 3 Sept
Graduate by Hilton Annapolis
The Westin Annapolis
View from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1005)
"The Hotel was very clean and convenient to everything that we wanted to do!!!!"
The price is Rp2.570.871
Rp2.930.793 total
includes taxes & fees
24 Aug - 25 Aug
The Westin Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (854)
" Very clean, spacious room, friendly staff"
The price is Rp3.834.478
Rp4.371.305 total
includes taxes & fees
24 Aug - 25 Aug
Annapolis Waterfront Hotel, Autograph Collection
DoubleTree by Hilton Hotel Annapolis
Garden

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1003)
"The Double Tree was a great place to stay! Great location amd the staff are very pleasant and helpful! "
The price is Rp1.539.450
Rp1.754.973 total
includes taxes & fees
31 Aug - 1 Sept
DoubleTree by Hilton Hotel Annapolis
The Inn at Chesapeake Bay Beach Club
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (410)
"Great location and amenities"
The price is Rp3.625.875
Rp4.434.688 total
includes taxes & fees
25 Aug - 26 Aug
The Inn at Chesapeake Bay Beach Club
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (34)
"Loved the Oaks! Fabulous accommodations and excellent staff"
The price is Rp6.657.107
Rp7.322.817 total
includes taxes & fees
17 Aug - 18 Aug
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 Rp9.240.583 per night from 7 Sept to 8 Sept
Rp9.240.583
Rp11.181.186 total
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (358 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
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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 Rp5.592.066

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.