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Hotels in Chester

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Check Last Minute Chester Hotel Deals

Tonight May 18 - May 19Next weekend May 23 - May 25

Choose from 1242 Chester Hotel Deals

Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
  • 12 min drive from Chesapeake Exploration Center
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,773 reviews)
"Loved everything about the inn."

Reviewed on May 16, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4 out of 5
126 West St, Annapolis, MD
  • 12 min drive from Chesapeake Exploration Center
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,003 reviews)
"The Graduate is a favorite of mine when visiting Annapolis, convenient walk to restaurants shops and downtown Annapolis. Easy parking on site. Friendly staff and nice rooms with decor of The United States Naval Academy."

Reviewed on May 14, 2025

Graduate by Hilton Annapolis
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3 out of 5
2600 Housley Road, Annapolis, MD
  • 15 min drive from Chesapeake Exploration Center
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,003 reviews)
"Comfortable"

Reviewed on May 13, 2025

Country Inn & Suites by Radisson, Annapolis, MD
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
  • 11 min walk from Chesapeake Exploration Center
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9.4/10 Exceptional! (540 reviews)
"From entry, the front desk staff, Charlene to be specific was amazing! She was friendly, insightful, informative AND our bar tender! Ms. Charlene DESERVES A RAISE! The hotel itself and our room was beautiful! Almost as beautiful as the view! I will definitely stay here again!"

Reviewed on May 15, 2025

Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
  • 12 min drive from Chesapeake Exploration Center
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,007 reviews)
"Great location, staff was kind and professional, the restaurant in the lobby had great food!"

Reviewed on May 13, 2025

Hilton Garden Inn Annapolis Downtown
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4 out of 5
210 Holiday Court, Annapolis, MD
  • 14 min drive from Chesapeake Exploration Center
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,002 reviews)
"Super clean. Nice stay"

Reviewed on May 3, 2025

DoubleTree by Hilton Hotel Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4 out of 5
80 Compromise St, Annapolis, MD
  • 11 min drive from Chesapeake Exploration Center
Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (819 reviews)
"The restaurant is closed for weeks (months?) but the staff is great and plenty of restaurants in easy walk."

Reviewed on May 4, 2025

Annapolis Waterfront Hotel, Autograph Collection
SpringHill Suites by Marriott Annapolis
SpringHill Suites by Marriott Annapolis
3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
  • 15 min drive from Chesapeake Exploration Center
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
9/10 Wonderful! (1,002 reviews)
"Loving"

Reviewed on May 11, 2025

SpringHill Suites by Marriott Annapolis
The Westin Annapolis
The Westin Annapolis
4 out of 5
100 Westgate Cir, Annapolis, MD
  • 12 min drive from Chesapeake Exploration Center
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,004 reviews)
"Great location and dining options near hotel. Definitely recommend!"

Reviewed on May 15, 2025

The Westin Annapolis
Courtyard by Marriott Annapolis
Courtyard by Marriott Annapolis
3 out of 5
2559 Riva Rd, Annapolis, MD
  • 15 min drive from Chesapeake Exploration Center
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,002 reviews)
Great place to stay
"Loved staying here"

Reviewed on May 14, 2025

Courtyard by Marriott Annapolis
Hilton Garden Inn Annapolis
Hilton Garden Inn Annapolis
3 out of 5
305 Harry S Truman Pkwy, Annapolis, MD
  • 15 min drive from Chesapeake Exploration Center
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,005 reviews)
"Staff was extremely kind and helpful. The room was clean and comfortable! It was a super easy and cheap uber into downtown Annapolis"

Reviewed on May 11, 2025

Hilton Garden Inn Annapolis
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
  • 15 min drive from Chesapeake Exploration Center
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (804 reviews)
"Average overall, rooms are a bit dated."

Reviewed on May 17, 2025

Sonesta ES Suites Annapolis
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.

Find cheap hotels in Chester

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Finding a cheap car rental deal in Chester is as easy as scoring cheap hotels in Chester. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.