Search for Cheap Deals onHotels in Chester
Choose from 1241 Chester Hotel Deals

Historic Inns of Annapolis
Reviewed on Jul 18, 2025

Graduate by Hilton Annapolis
Reviewed on Jul 14, 2025

DoubleTree by Hilton Hotel Annapolis
Reviewed on Jul 10, 2025

Country Inn & Suites by Radisson, Annapolis, MD
Reviewed on Jul 18, 2025

Annapolis Waterfront Hotel, Autograph Collection
Reviewed on Jul 9, 2025

Hilton Garden Inn Annapolis Downtown
Reviewed on Jul 15, 2025

Best Western Annapolis
Reviewed on Jul 17, 2025

SpringHill Suites by Marriott Annapolis
Reviewed on Jul 15, 2025

Hilton Garden Inn Annapolis
Reviewed on Jul 8, 2025

Courtyard by Marriott Annapolis
Reviewed on Jul 14, 2025

Sonesta ES Suites Annapolis
Reviewed on Jul 17, 2025

Fairfield Inn & Suites By Marriott Annapolis
Reviewed on Jul 14, 2025
Find cheap hotels in Chester
You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Chester hotel with Hotwire to complete your one-of-a-kind travel checklist.
For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chester.
Choosing the right hotel in Maryland has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chester’s 1,241 hotels. Choose the one that best catches your trip’s tourist drift.
If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $93. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Chester hotel deals at the last minute.
While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Chester. No matter your reason for visiting Chester, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.
Frequently Asked Questions About Chester hotels
Where can I find the best last-minute travel deals?
If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Chester for as low as $93.
How many hotels are there in Chester?
With over 1,241 hotels in Chester, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $93.
How to find cheap car rentals in Chester?
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.
Top Booked Hotels in Chester
- Historic Inns of Annapolis
- Graduate by Hilton Annapolis
- DoubleTree by Hilton Hotel Annapolis
- Country Inn & Suites by Radisson, Annapolis, MD
- Annapolis Waterfront Hotel, Autograph Collection
- Hilton Garden Inn Annapolis Downtown
- Best Western Annapolis
- SpringHill Suites by Marriott Annapolis
- Hilton Garden Inn Annapolis
- Courtyard by Marriott Annapolis
- Sonesta ES Suites Annapolis
- The Westin Annapolis
- Crowne Plaza Annapolis by IHG
- St Michaels Inn
- Hotels near Chesapeake Exploration Center
- Hotels near U.S. Naval Academy
- Hotels near Annapolis City Dock
- Hotels near Chesapeake Bay Bridge
- Hotels near Sandy Point State Park
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Anne Arundel Medical Center
- Hotels near Westfield Annapolis Mall
- Hotels near St. Michaels Winery
- Hotels near Rock Hall Harbor
- Hotels near Annapolis Harbor Center Shopping Center
- Hotels near Annapolis Mall Shopping Center
- Hotels near Maryland Quiet Waters Park
- Hotels near Annapolis Maritime Museum
- Hotels near Queenstown Premium Outlets
- Hotels near Maryland State House
- Hotels near Chesapeake Bay Maritime Museum
- Hotels near William Paca House
- Hotels near Annapolis Harbour Center
- Hotels near Queenstown Harbor Golf Club
- Annapolis Hotels
- St. Michaels Hotels
- Cambridge Hotels
- Easton Hotels
- Chesapeake Beach Hotels
- Chesapeake Bay Hotels
- Grasonville Hotels
- Stevensville Hotels
- Glen Burnie Hotels
- Eastern Shore Hotels
- North Beach Hotels
- Chestertown Hotels
- Deale Hotels
- Rock Hall Hotels
- Tilghman Hotels
- Edgewater Hotels
- Pasadena Hotels
- Shady Side Hotels
- Oxford Hotels
- Gambrills Hotels