Photo by Patricia Knorr

Find 4 Star Hotels in Chester, MD from SAR 384

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Compare Chester 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Graduate by Hilton Annapolis
Reception

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1010)
"The staff was the best always checking to see if I needed anything. "
The price is SAR 494
SAR 563 total
includes taxes & fees
24 Dec - 25 Dec
Graduate by Hilton Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Exterior

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (776)
"All good "
The price is SAR 778
SAR 887 total
includes taxes & fees
1 Dec - 2 Dec
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, (1010)
"Great hotel experience all the way around !"
The price is SAR 384
SAR 438 total
includes taxes & fees
30 Nov - 1 Dec
DoubleTree by Hilton Hotel Annapolis
The Westin Annapolis
Exterior

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1031)
"Great experience overall!"
The price is SAR 653
SAR 745 total
includes taxes & fees
20 Dec - 21 Dec
The Westin 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, (367)
"Friendly staff and great eating options. "
The price is SAR 785
SAR 967 total
includes taxes & fees
1 Dec - 2 Dec
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, (56)
"delightful and charming! great views and peaceful! We really enjoyed our stay!"
The price is SAR 1,348
SAR 1,483 total
includes taxes & fees
8 Dec - 9 Dec
The Oaks Waterfront
The Annapolis Inn
Room

The Annapolis Inn

4.0 star property
9.0 out of 10, Wonderful, (4)
"The Annapolis Inn exceed every expectation! The owners are absolutely fabulous. The property is gorgeous and exceptionally appointed. Alex is a gourmet chef who left us wanting more each breakfast. Joe is a tremendous story teller and you will want to sit for hours listening and conversing. Both are wonderful and kind humans who gave us their undivided attention and complete care. This was my first experience at a bed and breakfast and I am forever spoiled. You won’t find better accommodations...
The Annapolis Inn
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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 SAR 1,075 per night from Dec 17 to Dec 18
SAR 1,075
SAR 1,293 total
includes taxes & fees
17 Dec - 18 Dec
9.4/10 Exceptional! (322 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.

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 favorite 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 SAR 952

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 accommodations. 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 travelers.
Does Chester have any 4-star all-inclusive resorts?
Finding your dream vacation in Chester is as easy as entering your dates and destination, and clicking on our “All inclusive” filter. Stay and play where almost everything is already taken care of like your accommodations, food, activities and entertainment, or opt for a standard 4-star resort in or around this popular destination.
What are the top 4-star hotels in downtown Chester?
Enjoy the sights with ease when you check in to The Inn at Chesapeake Bay Beach Club. About 5 kilometers west from downtown Chester, this 4-star hotel offers the perfect spot to make the most of this buzzing city with the added convenience of Frette Italian sheets and a cafe.