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Find 4 Star Hotels in Chester, MD from $114

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

View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1067)
"Lovely hotel - everything was perfect except the coffee situation. Rubbish provision in room and then had to pay in the lobby."
The price is $195
$222 total
includes taxes & fees
May 26 - May 27
Graduate Annapolis
Room, 2 Queen Beds, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
9.0 out of 10, Wonderful, (706)
"…"
The price is $247
$282 total
includes taxes & fees
May 27 - May 28
Annapolis Waterfront Hotel, Autograph Collection
Lobby
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1001)
"Great property. Easy location. Close to everything. Nice room. Comfortable bed. Walls a little thin. Could hear neighbors. Would stay again. "
The price is $114
$130 total
includes taxes & fees
May 7 - May 8
DoubleTree by Hilton Hotel Annapolis
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Exterior
The Westin Annapolis
4.0 star property
8.6 out of 10, Excellent, (1000)
"Great time. "
The price is $169
$193 total
includes taxes & fees
May 12 - May 13
The Westin Annapolis
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (340)
"Everyone was so friendly including the manager. We had a great experience and I cant wait to go back soon. "
The price is $239
$291 total
includes taxes & fees
May 6 - May 7
The Inn at Chesapeake Bay Beach Club
Front of property
The Oaks Waterfront
4.0 star property
9.8 out of 10, Exceptional, (45)
"Beautiful property, loved it!"
The Oaks Waterfront
Horseback riding
The Inn at Tacaro Estate
4.5 star property
8.0 out of 10, Very Good, (4)
"It was amazing. The place was nicely decorated. Food was great. Highly recommended."
The price is $367
$419 total
includes taxes & fees
May 2 - May 3
The Inn at Tacaro Estate
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

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 $554 per night from May 2 to May 3
$554
$670 total
includes taxes & fees
May 2 - May 3
9.4/10 Exceptional! (292 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.

Chester Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Chester, Maryland are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Chester 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Chester. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Chester, Maryland, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Chester hotels offer everything your heart desires.

Frequently asked questions

What are the best 4-star hotels in Chester?
Expedia customers highly rate The Inn at Chesapeake Bay Beach Club. From its handy amenities to its welcoming staff, everything about this 4-star hotel in Chester is designed to provide an exceptional vacation experience.
How much does it cost to stay in a 4-star hotel in Chester?
With Expedia’s filter tool, scoring an awesome deal on a 4-star hotel in Chester just got simpler. Start by entering your chosen arrival date and length of your escape. Then list the results by price and pick a property that best matches your budget and style.

  • Search for the lowest price from $554

What's the difference between 5-star and 4-star hotels in Chester?
Offering an inviting traveler experience and upmarket décor, 4-star hotels are a fabulous option for your Chester getaway. These kinds of stays generally feature lots of handy amenities that make it easy to kick back and relax — think complimentary bathrobes, restaurants and pools. Or get a taste of the high life at a 5-star hotel designed to pamper with luxury perks and amenities. Round-the-clock concierge service, premium toiletries and world-class dining are typically included at these deluxe retreats.
Does Chester have any 4-star all-inclusive resorts?
Finding your dream hotel in Chester is as simple as entering your travel dates and destination, and selecting our “All inclusive” filter. Stay and play where just about everything is already taken care of like your room, meals and activities, or opt for a standard 4-star resort in or around this sought-after destination.
Are there any 4-star casino hotels in Chester?
Shuffle between your room and the slot machines with ease by using our handy filters to find 4-star casino hotels in and around Chester. Celebrating with someone special? Refine your search further by selecting amenities with a wow-factor, like a pool or view.
What are the top 4-star hotels in downtown Chester?
Situated around 3 mi west from the heart of Chester, The Inn at Chesapeake Bay Beach Club will put you close to the action. This 4-star hotel also has a cafe and a pillowtop mattress for your convenience.

Recent reviews of Chester hotels
Expedia verified reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

5/5 Excellent
"It was really nice that the hotel offers a local shuttle for free. It was so convenient and easy to get into town."
A verified traveler from Harrisburg stayed at DoubleTree by Hilton Hotel Annapolis
Posted 3 days ago
DoubleTree by Hilton Hotel Annapolis