Photo by Patricia Knorr

Find 4 Star Hotels in Chester, MD from SAR816

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

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

Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1022)
"We had a nice time for our baby moon!"
The price is SAR 668
SAR 761 total
includes taxes & fees
1 Jul - 2 Jul
1 Raj. - 2 Raj.
Graduate Annapolis
The Westin Annapolis
4.0 star property
8.6 out of 10, Excellent, (1000)
"great"
The price is SAR 765
SAR 873 total
includes taxes & fees
8 Jul - 9 Jul
8 Raj. - 9 Raj.
The Westin Annapolis
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1001)
"It’s a ridiculously long trip from the lobby to the 6th of the north tower but easy going. The pool is huge for a hotel. The staff was far beyond courteous and friendly. "
The price is SAR 427
SAR 487 total
includes taxes & fees
1 Jul - 2 Jul
1 Raj. - 2 Raj.
DoubleTree by Hilton Hotel Annapolis
Save an average of 15% on thousands of hotels when you're signed in
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
9.0 out of 10, Wonderful, (718)
"Beautiful upscale accommodations. Within walking distance to everything you'll want to see and do. You want a view and a high level of service, then you'll pay for it. Loved the vallet setvice so quick and easy. That is the only option you have at this hotel. Downtown and Historic Annapolis are so pretty with lots of shops and eateries. Lots of taverns too if you travel with no kids. View of the Chesapeake Bay and Bridge. "
The price is SAR 897
SAR 1,023 total
includes taxes & fees
7 Jul - 8 Jul
7 Raj. - 8 Raj.
Annapolis Waterfront Hotel, Autograph Collection
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (345)
"The Inn is a wonderful place - very nice atmosphere, and excellent attentive service. What I liked best is that it was peaceful. I went for a peaceful get-away - and I especially loved the balmy air, the gentle breezes, the gardens, and the birds. Heard and saw so many wonderful birds! And you can meander around the surrounding lanes, and end up down by the water. All so nice!"
The price is SAR 934
SAR 1,133 total
includes taxes & fees
7 Jul - 8 Jul
7 Raj. - 8 Raj.
The Inn at Chesapeake Bay Beach Club
The Oaks Waterfront
4.0 star property
9.8 out of 10, Exceptional, (50)
"Everything was outstanding. We will be back."
The price is SAR 1,497
SAR 1,647 total
includes taxes & fees
20 Jun - 21 Jun
20 Jum. II - 21 Jum. II
The Oaks Waterfront
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 SAR 1,450
SAR 1,653 total
includes taxes & fees
15 Jul - 16 Jul
15 Raj. - 16 Raj.
The Inn at Tacaro Estate
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.
Still don't see what you're looking for?
See all properties in Chester.
You can also use these popular filters to refine your search.
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 SAR816

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.

Recent reviews of Chester hotels
Expedia verified reviews