Find 4 Star Hotels in Chester, MD from SAR 335

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Check prices for these dates

Tonight
13 Nov - 14 Nov
Tomorrow
14 Nov - 15 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

Our top choices for Chester 4-star hotels

A spacious atrium with a high ceiling, skylights, and a patterned floor.

1. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,001 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is SAR 489
SAR 558 total
includes taxes & fees
29 Nov - 30 Nov
Graduate by Hilton Annapolis
A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

2. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,278 reviews)
"i enjoyed how close the place was to many local shops and resturants."
United States
michel demanche
The price is SAR 335
SAR 382 total
includes taxes & fees
13 Dec - 14 Dec
DoubleTree by Hilton Hotel Annapolis
A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.

3. 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, (514 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is SAR 679
SAR 850 total
includes taxes & fees
9 Dec - 10 Dec
The Inn at Chesapeake Bay Beach Club
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

4. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,000 reviews)
"Excellent location, Very nice Hotel"
United States
Loraine
The price is SAR 597
SAR 680 total
includes taxes & fees
6 Dec - 7 Dec
The Westin Annapolis
A balcony with a table set for two, overlooking a marina with boats.

5. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
United States
Donna
The price is SAR 808
SAR 921 total
includes taxes & fees
23 Nov - 24 Nov
Annapolis Waterfront Hotel, Autograph Collection
A two-story house with a front porch, white siding, and a black front door.

6. The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (46 reviews)
"Absolutely perfect little 3 day get away. The entire atmosphere was excellent, great complementary breakfast from menu, beautiful modern rooms, perfectly manicured landscaping with lots of seating for relaxing by the water. The entire staff were so friendly and helpful. We made an excellent choice and would definitely go back. 10+ out of 10."
United States
William
The price is SAR 1,652
SAR 1,817 total
includes taxes & fees
15 Nov - 16 Nov
The Oaks Waterfront

Top Chester Hotel Reviews

A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville

10/10 Excellent

Beautiful place, quiet and clean.
United States
Chuck
Reviewed May 15, 2025
The Inn at Chesapeake Bay Beach Club

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 335

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.