Search for Cheap Deals onHotels in Chester
Check Last Minute Chester Hotel Deals
Choose from 1193 Chester Hotel Deals
Historic Inns of Annapolis
"Wonderful location and beautiful historic place. Staff is very welcoming and helpful. I do miss the chilled water that was previously available in the afternoons, it was always a treat after the walk back to the hotel, please consider bringing it back."
Reviewed on Jul 8, 2026
DoubleTree by Hilton Hotel Annapolis
"We had an average stay. The hotel itself is a bit dated - needs renovation and updates. Our room had an odor - like mildew. The front desk staff is underwhelming. Lacked energy and friendliness and didn't want to be bothered honestly. However, the wait staff at breakfast in the restaurant were great. ..."
Reviewed on Jul 8, 2026
Crowne Plaza Annapolis by IHG
"From checking to check out it was a great experience with staff and the accommodations. Thanks the Spillers"
Reviewed on Jul 8, 2026
Country Inn & Suites by Radisson, Annapolis, MD
"The jacuzzi tub didn't work so it was basically a soaking tub. We Still enjoyed it but I have seen . Other reviewers say the same thing. So"
Reviewed on Jul 6, 2026
Graduate by Hilton Annapolis
St Michaels Inn
"A great and affordable alternative to get away from the grind and close to the water. It was our anniversary, and we enjoyed having a pool on 100-degree days and a cool room. St. Michaels is a quaint and fun town to visit. We've stayed here several times and will be back."
Reviewed on Jul 8, 2026
Hilton Garden Inn Annapolis Downtown
"The room was small and musty. Repairs to walls in the bathroom not finished. No air conditioning in the fitness room - and the peloton display wasn’t working. Also, no water cups or towels in the fitness room. Parking wasn’t available so we had to go down the street. Not up to Hilton standards at ..."
Reviewed on Jul 5, 2026
The Westin Annapolis
"The front desk staff was very helpful"
Reviewed on Jul 7, 2026
Courtyard by Marriott Annapolis
"The person that checked me was super dry and seemed to have an attitude while checking me in. The pool itself was so dirty and the water was not super clear, instead it was a bit cloudy. The shower in the pool looked disgusting and had the inside of a wet diaper all spread through the front of it ..."
Reviewed on Jul 7, 2026
Annapolis Waterfront Hotel, Autograph Collection
"everything was great, esp staff!"
Reviewed on Jul 6, 2026
Best Western Kent Narrows Inn
"The place is seriously dated and in need of upgrades. My curtains were torn and unusable and with the sun beating in on one of those 100 degree days I was nonplussed. A quick discussion with the very accommodating desk clerk had the curtain “fixed” in no time (still needed replacement because it ..."
Reviewed on Jul 3, 2026
Hilton Garden Inn Kent Island Marina
"Kitchen closed for dinner due to staff shortage and food was on the floor in the dinning area for two days."
Reviewed on Jul 3, 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 1,193 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 $116. 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 $116.
How many hotels are there in Chester?
With over 1,193 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 $116.
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.
- Hotels near Chesapeake Exploration Center
- Hotels near U.S. Naval Academy
- Hotels near Chesapeake Bay
- Hotels near Sandy Point State Park
- Hotels near Annapolis City Dock
- Hotels near Chesapeake Bay Bridge
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Westfield Annapolis Mall
- Hotels near Anne Arundel Medical Center
- Hotels near Maryland State House
- Hotels near Queenstown Premium Outlets
- Hotels near Annapolis Harbor Center Shopping Center
- Hotels near Queenstown Harbor Golf
- Hotels near Maryland Quiet Waters Park
- Hotels near Annapolis Mall Shopping Center
- Hotels near Northern Chesapeake Bay
- Hotels near St. Michaels Winery
- Hotels near Chesapeake Bay Maritime Museum
- Hotels near Annapolis Maritime Museum
- Hotels near Rock Hall Harbor
- Annapolis Hotels
- St. Michaels Hotels
- Chesapeake Beach Hotels
- Easton Hotels
- Stevensville Hotels
- Grasonville Hotels
- Glen Burnie Hotels
- Eastern Shore Hotels
- Chestertown Hotels
- North Beach Hotels
- Rock Hall Hotels
- Pasadena Hotels
- Tilghman Hotels
- Edgewater Hotels
- Oxford Hotels
- Essex Hotels
- Severna Park Hotels
- Arnold Hotels
- Gambrills Hotels
- Queenstown Hotels
