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DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG
"I wish I could give half stars because this place is really a 4.5 stars. First off this place was great, it is everything you need for a hotel. Great prices, friendly staff, very clean, very nice hotel. Why I gave it 4 stars? The coffee machine was down for our first night, the jacuzzi was down for ..."
Reviewed on Aug 25, 2026
Graduate by Hilton Annapolis
"I arrived late following a long-distance sailboat race across the Chesapeake Bay. “Nick” was managing the front desk. He was polite, efficient, friendly, and professional. He offered me the best room the hotel had available at my price, and guaranteed I would have a good night’s rest. He was 100% ..."
Reviewed on Aug 25, 2026
St Michaels Inn
"This is the 2nd time we've stayed at the St Michaels Inn, but the last time was 6 years ago. They are in the middle of renovating but I will say the room was clean and fairly updated. The breakfast was just like you'd see at most hotels and had plenty of seating. Parking was easy and we were in the ..."
Reviewed on Aug 25, 2026
Country Inn & Suites by Radisson, Annapolis, MD
"There wasn’t a fan in the bathroom. Very good location in Annapolis."
Reviewed on Aug 23, 2026
Annapolis Waterfront Hotel, Autograph Collection
Hilton Garden Inn Annapolis Downtown
Courtyard by Marriott Annapolis
"Just ok"
Reviewed on Aug 24, 2026
Hyatt Place Kent Narrows & Marina
"our ocean facing room was beautiful. We enjoyed staying here."
Reviewed on Aug 24, 2026
Holiday Inn Express & Suites Annapolis by IHG
"Perfect for what I needed"
Reviewed on Aug 21, 2026
The Westin Annapolis
"The beds were so comfortable"
Reviewed on Aug 25, 2026
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 1,195 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 $109. 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 $109.
How many hotels are there in Chester?
With over 1,195 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 $109.
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.
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