Search for Cheap Deals onHotels in Chester
Choose from 1207 Chester Hotel Deals
Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis
"I booked a room and paid. When I arrived at the hotel, I was told no rooms was available. I still haven't received my money back. I called hotels.com and still no action. I was ripped off! The manager at the hotel lied and said I didn't come. I had to give details on who I spoke too, what I saw and ..."
Reviewed on Oct 10, 2026
Crowne Plaza Annapolis by IHG
Historic Inns of Annapolis
St Michaels Inn
"We travel to St micheals md, several times a year, during the oyster season. Usually we stay at hotels in easton, so this time we tried the st micheals inn. It's closer to the Cheasapeake Landing restaurant. We were placed in a room opposite the main street, which made for a very quiet evening. Much ..."
Reviewed on Oct 10, 2026
Hilton Garden Inn Annapolis Downtown
"Hotel is overrated. The cost of a similar hotel in any other decent city is at least 20-25% lower. The walls between rooms are probably made of a cardboard, and you can hear your neighbors like if they were staying behind a curtain. They charge $35 per night for self-parking in a crimped lot. Breakfast ..."
Reviewed on Oct 9, 2026
Sonesta ES Suites Annapolis
Courtyard by Marriott Annapolis
Annapolis Waterfront Hotel, Autograph Collection
"We’ve stayed at Marriott waterfront for over 10 yrs & this was the worst stay. The air conditioning didn’t work & we had a portable ac unit that was so loud I couldn’t sleep. The elevators didn’t work half the time & my husband had to walk to Starbucks that’s not really close for coffee every morning. ..."
Reviewed on Oct 11, 2026
The Inn at Chesapeake Bay Beach Club
"Had an amazing stay here. The room was spotlessly clean from top to bottom. The linens were fresh, the bathroom was pristine, and everything felt completely sanitized. It’s rare to find a property that pays such close attention to detail. Fantastic housekeeping service!"
Reviewed on Oct 10, 2026
The Westin Annapolis
"Easy parking. Super comfy bed."
Reviewed on Oct 9, 2026
Best Western Annapolis
Find cheap hotels in Chester
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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 1,207 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 $90. 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 $90.
How many hotels are there in Chester?
With over 1,207 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 $90.
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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.
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