Photo by Patricia Knorr

Find 4 Star Hotels in Chester, MD from SAR 347

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Check availability on Chester 4 Star Hotels

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

DoubleTree by Hilton Hotel Annapolis
Lobby

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1003)
"Comfortable and clean hotel. Staff was very friendly and receptive. TV was great and shower which included body wash, shampoo, and conditioner was nice. My only issue is that Hotels.com advertised 50$ pet fee which wasn’t honored. Charged 75$. "
The price is SAR 347
SAR 396 total
includes taxes & fees
3 Mar - 4 Mar
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1006)
"Great hotel! Very clean room and common areas. The staff was extremely friendly and accommodating and the location was perfect! Easily walkable to restaurant, bars, shopping and morning coffee! "
The price is SAR 571
SAR 650 total
includes taxes & fees
16 Mar - 17 Mar
Graduate by Hilton Annapolis
The Westin Annapolis
City view from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (999)
"I would have given it an overall excellent review except for the construction. Room was comfy and clean."
The price is SAR 634
SAR 722 total
includes taxes & fees
28 Feb - 1 Mar
The Westin Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (799)
"Perfect anniversary staycation! Our only issue was the temperature in the room could not be easily regulated. "
The price is SAR 762
SAR 868 total
includes taxes & fees
16 Mar - 17 Mar
Annapolis Waterfront Hotel, Autograph Collection
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, (374)
"Great spot!"
The price is SAR 671
SAR 840 total
includes taxes & fees
2 Mar - 3 Mar
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, (57)
" Beautiful property, wonderful staff, excellent food service."
The price is SAR 1,448
SAR 1,593 total
includes taxes & fees
12 Mar - 13 Mar
The Oaks Waterfront
The Annapolis Inn
Luxury Suite, Garden View (Rutland Suite) | Egyptian cotton sheets, premium bedding, pillowtop beds

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 1,126 per night from Mar 5 to Mar 6
SAR 1,126
SAR 1,363 total
includes taxes & fees
5 Mar - 6 Mar
9.4/10 Exceptional! (331 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 957

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.