Search for Cheap Deals on
Hotels in Chester

Photo by Patricia Knorr

Last Minute Hot Rate® Hotel Deals in Chester

We Hide Hotel Names So You Can Find 4-Star Hotels At 2-Star Prices. Choose the Location, Star Rating & Amenities. Let Hotwire Find You the Best Deal. Book Today!

Choose from 1184 Chester Hotel Deals

Admiral Suites
Admiral Suites
2.5 out of 5
120 Admiral Cochrane Dr, Edgewater, MD
  • 15 min drive from Chesapeake Exploration Center
The price is $89 per night from May 28 to May 29
$89
per night
May 28 - May 29
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
6.6/10 (157 reviews)
Pet friendly, quiet
"Fairly good. Very basic room. everything worked Very quiet room in nice area. Great pet walking areas. renovations underway Very good coffee"

Reviewed on May 18, 2024

Admiral Suites
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
The price is $159 per night from May 28 to May 29
$159
per night
May 28 - May 29
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! (1,617 reviews)
"Myra at checkin was great!!!"

Reviewed on May 25, 2024

Historic Inns of Annapolis
Crowne Plaza Annapolis, an IHG Hotel
Crowne Plaza Annapolis, an IHG Hotel
3.5 out of 5
173 Jennifer Rd, Annapolis, MD
  • 14 min drive from Chesapeake Exploration Center
The price is $126 per night from May 29 to May 30
$126
per night
May 29 - May 30
Book a stay at this 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! (1,004 reviews)
"Hhgggggg"

Reviewed on May 24, 2024

Crowne Plaza Annapolis, an IHG Hotel
Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
  • 12 min drive from Chesapeake Exploration Center
The price is $195 per night from Jun 9 to Jun 10
$195
per night
Jun 9 - Jun 10
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
9.2/10 Wonderful! (1,045 reviews)
"Hotel was convenient to the historic area. Parking lot was as too far from the main entrance."

Reviewed on May 23, 2024

Graduate 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
The price is $129 per night from May 28 to May 29
$129
per night
May 28 - May 29
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (624 reviews)
"Clean and comfortable. Good safe location"

Reviewed on May 24, 2024

Sonesta ES Suites 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
The price is $101 per night from Jun 17 to Jun 18
$101
per night
Jun 17 - Jun 18
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 ...
8.8/10 Excellent! (1,004 reviews)
"Comfortable, clean, friendly"

Reviewed on May 21, 2024

Country Inn & Suites by Radisson, Annapolis, MD
The Westin Annapolis
The Westin Annapolis
4 out of 5
100 Westgate Cir, Annapolis, MD
  • 12 min drive from Chesapeake Exploration Center
The price is $204 per night from Jun 2 to Jun 3
$204
per night
Jun 2 - Jun 3
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 and the clean ...
8.6/10 Excellent! (1,002 reviews)
"Great location!"

Reviewed on May 25, 2024

The Westin Annapolis
Hilton Garden Inn Annapolis
Hilton Garden Inn Annapolis
3 out of 5
305 Harry S Truman Pkwy, Edgewater, MD
  • 15 min drive from Chesapeake Exploration Center
The price is $113 per night from Jun 2 to Jun 3
$113
per night
Jun 2 - Jun 3
Stay at this 3-star business-friendly hotel in Edgewater. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,002 reviews)
Very Good Hotel but Needs some cleaning.
"The staff was wonderful. However, the safe in the room did not work, the bartender was out so no bar in the lobby, carpeting throughout hotel needed cleaning and there should have been a safety bar on the jacuzzi tub. The location was very convenient. There were no channel guides in the room nor ..."

Reviewed on May 23, 2024

Hilton Garden Inn Annapolis
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
The price is $127 per night from Jun 2 to Jun 3
$127
per night
Jun 2 - Jun 3
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)
"I really enjoyed my staying, the only thing it didn't work was my room's phone to call the main lobby. Other than that was good."

Reviewed on May 24, 2024

DoubleTree by Hilton Hotel Annapolis
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
The price is $139 per night from May 28 to May 29
$139
per night
May 28 - May 29
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
8.6/10 Excellent! (849 reviews)
"Beds were super clean and comfortable. The stay was pleasant. The bartender on Thursday night was not very accommodating"

Reviewed on May 13, 2024

Hilton Garden Inn Annapolis Downtown
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
The price is $139 per night from May 30 to May 31
$139
per night
May 30 - May 31
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! (1,001 reviews)
"Close to highways, ease into Annapolis proper and clean property. Staff are kind and the hotel is well maintained."

Reviewed on May 23, 2024

SpringHill Suites by Marriott Annapolis
St Michaels Inn
St Michaels Inn
2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
  • 35 min drive from Chesapeake Exploration Center
The price is $112 per night from Jun 2 to Jun 3
$112
per night
Jun 2 - Jun 3
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,003 reviews)
Nice room is a beautiful town
"The room was in good shape. The staff was friendly, especially the lady that took care of breakfast."

Reviewed on May 19, 2024

St Michaels Inn
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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

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 1,184 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 $79. 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 up to 60% 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 save up to 60% off 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 $79.

How many hotels are there in Chester?

With over 1,184 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 $79.

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 even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Chester now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Chester right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.