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Hotels in Chester

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Tonight Apr 6 - Apr 7Next weekend Apr 11 - Apr 13

Choose from 1197 Chester Hotel Deals

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 Apr 20 to Apr 21
$101
includes taxes & fees
Apr 20 - Apr 21
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! (1,001 reviews)
Friendly stay
"We enjoyed our stay in Annapolis. The location of the hotel was great. I liked being in a quiet area. Ashely at the front desk was so friendly and welcoming. The staff were all nice. The hot breakfast was good and just right. Our room temperature and just right. It was a good two-night stay"

Reviewed on Mar 31, 2025

Country Inn & Suites by Radisson, Annapolis, MD
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 $199 per night from Apr 13 to Apr 14
$199
includes taxes & fees
Apr 13 - Apr 14
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! (1,735 reviews)
"I had a lovely stay at The Maryland Inn. The front desk staff were very friendly both during check in and check out. The accommodations were quite comfortable. I would definitely stay here again!"

Reviewed on Apr 1, 2025

Historic Inns of Annapolis
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 $170 per night from Apr 9 to Apr 10
$170
includes taxes & fees
Apr 9 - Apr 10
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 in our reviews. ...
8.6/10 Excellent! (1,001 reviews)
"Always love our Westin Annapolis stay - can’t wait to see it post construction"

Reviewed on Apr 2, 2025

The Westin Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4 out of 5
80 Compromise St, Annapolis, MD
  • 11 min drive from Chesapeake Exploration Center
The price is $218 per night from Apr 20 to Apr 21
$218
includes taxes & fees
Apr 20 - Apr 21
Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (808 reviews)
"Good"

Reviewed on Mar 23, 2025

Annapolis Waterfront Hotel, Autograph Collection
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG
3.5 out of 5
173 Jennifer Rd, Annapolis, MD
  • 14 min drive from Chesapeake Exploration Center
The price is $119 per night from Apr 15 to Apr 16
$119
includes taxes & fees
Apr 15 - Apr 16
Stay at this 3.5-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,003 reviews)
Annapolis
"We have stayed here before and normally everyone is friendly. Not this time. I won’t go into details but the front desk was rude during our stay. Room seemed to be clean and comfortable."

Reviewed on Apr 3, 2025

Crowne Plaza Annapolis by IHG
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 $106 per night from Apr 20 to Apr 21
$106
includes taxes & fees
Apr 20 - Apr 21
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 ...
8.4/10 Very Good! (1,002 reviews)
"Hotel is close to everything, mall, food, shopping"

Reviewed on Mar 31, 2025

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 $96 per night from Apr 20 to Apr 21
$96
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,002 reviews)
"My only complaint was my room was near the elevator, ice machines, roof access where there was some repairs or renovation that week."

Reviewed on Apr 4, 2025

Hilton Garden Inn Annapolis Downtown
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
  • 11 min walk from Chesapeake Exploration Center
The price is $159 per night from Apr 13 to Apr 14
$159
includes taxes & fees
Apr 13 - Apr 14
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9.4/10 Exceptional! (513 reviews)
"Front desk staff was VERY nice."

Reviewed on Mar 28, 2025

Hyatt Place Kent Narrows & Marina
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 $108 per night from Apr 28 to Apr 29
$108
includes taxes & fees
Apr 28 - Apr 29
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (788 reviews)
"Stayed here over the weekend. What stood out is how clean the place felt. Smells great also"

Reviewed on Mar 31, 2025

Sonesta ES Suites Annapolis
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 $130 per night from Apr 7 to Apr 8
$130
includes taxes & fees
Apr 7 - Apr 8
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! (1,004 reviews)
"excellent accommodations and service"

Reviewed on Apr 4, 2025

SpringHill Suites by Marriott Annapolis
Courtyard by Marriott Annapolis
Courtyard by Marriott Annapolis
3 out of 5
2559 Riva Rd, Annapolis, MD
  • 15 min drive from Chesapeake Exploration Center
The price is $106 per night from Apr 13 to Apr 14
$106
includes taxes & fees
Apr 13 - Apr 14
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.4/10 Very Good! (991 reviews)
"Fast checking in. Queit area."

Reviewed on Apr 4, 2025

Courtyard by Marriott Annapolis
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4 out of 5
126 West St, Annapolis, MD
  • 12 min drive from Chesapeake Exploration Center
The price is $173 per night from Apr 14 to Apr 15
$173
includes taxes & fees
Apr 14 - Apr 15
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,001 reviews)
"I loved my stay here!"

Reviewed on Mar 31, 2025

Graduate by Hilton Annapolis
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.

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 1,197 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 $96. 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.

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Frequently Asked Questions About Chester hotels

Where can I find the best last-minute travel deals?

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How many hotels are there in Chester?

With over 1,197 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 $96.

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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.