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

Compare and book 4 Star 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 2.658.424 ₫
3.030.604 ₫ 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 5.655.886 ₫
6.447.710 ₫ total
includes taxes & fees
25 Aug - 26 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 3.844.531 ₫
4.382.765 ₫ 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 4.444.024 ₫
5.066.188 ₫ total
includes taxes & fees
9 Aug - 10 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 5.667.628 ₫
6.959.681 ₫ 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 11.566.708 ₫
12.723.379 ₫ total
includes taxes & fees
5 Aug - 6 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 16.321.122 ₫ per night from 23 Aug to 24 Aug
16.321.122 ₫
17.953.234 ₫ 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!

See all hotels in Chester
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Super quiet. Great bed."
Gary 1-night trip
Posted 1 hour ago
Graduate by Hilton Annapolis

Frequently asked questions

What are the best 4-star hotels in Chester?
Relax in upmarket comfort at The Inn at Chesapeake Bay Beach Club. According to reviews by our customers, this is one of Chester's favourite 4-star hotels.
How much does it cost to stay in a 4-star hotel in Chester?
Expedia can help you easily track down the ideal 4-star hotel for your getaway in Chester. Use our handy filter tool to fine-tune your search by things like budget, amenities and star rating and get access to fantastic deals in a few clicks.

  • Search for the lowest price from 10.202.147 ₫

What's the difference between 5-star and 4-star hotels in Chester?
If you decide to stay at a 4-star hotel in Chester, you'll typically find plenty of amenities to keep you relaxed, such as a pool, restaurant and gym. You can enjoy high-quality service and upmarket accommodation. Opt for a 5-star hotel and you'll have access to a few more perks — think on-site spas, around-the-clock concierge and indulgent turndown services. You're likely to get extra amenities and first-class services at a 5-star retreat, though both are terrific options for luxury travellers.