A boat docked at a pier during twilight with a city skyline in the background.

Chester Hotel Guide - 4 Stars Hotels in Chester, Maryland

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Check availability on Chester 4 Star Hotels

This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Chester 4-star hotels

Reception

1. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,076 reviews)
"Great hotel for the price"
United States
eliana
The price is Rp1.823.431
Rp2.078.712 total
includes taxes & fees
30 Aug - 31 Aug
DoubleTree by Hilton Hotel Annapolis
Premium bedding, down duvets, pillow-top beds, in-room safe

2. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (960 reviews)
"Wonderful stay! Excellent location on the water. Had a room with a balcony. Staff and restaurants were all very nice."
United States
Stacey
The price is Rp4.016.930
Rp4.579.299 total
includes taxes & fees
30 Aug - 31 Aug
Annapolis Waterfront Hotel, Autograph Collection
View from property

3. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,006 reviews)
"Comfortable beds! Really cute decor and very clean! The restaurant was delicious and the coffee shop great!"
United States
MARIANNA
The price is Rp2.636.990
Rp3.006.183 total
includes taxes & fees
23 Aug - 24 Aug
Graduate by Hilton Annapolis
Lobby

4. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,002 reviews)
"Clean room, great customer service and very nice people. The hotel is stunning"
United States
Jessica
The price is Rp3.581.403
Rp4.082.799 total
includes taxes & fees
6 Aug - 7 Aug
The Westin Annapolis
Front of property – evening/night

5. 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, (475 reviews)
"helpful staff, nice rooms"
United Kingdom
Jamie
The price is Rp3.887.464
Rp4.773.693 total
includes taxes & fees
31 Aug - 1 Sept
The Inn at Chesapeake Bay Beach Club
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

6. The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (43 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is Rp7.920.480
Rp8.712.528 total
includes taxes & fees
11 Aug - 12 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 Rp11.176.137 per night from 23 Aug to 24 Aug
Rp11.176.137
Rp12.293.752 total
23 Aug - 24 Aug
includes taxes & fees
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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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A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Great experience"
Chimezie 4-night trip
Posted 14 hours ago
The Westin Annapolis

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 Rp6.986.075

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.