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Hotels in Chester

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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
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! (1,001 reviews)
Very nice and neat hotel in good location. Staff are wonderful

Reviewed on Jan 7, 2026

DoubleTree by Hilton Hotel 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
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 bar and ...
9.2/10 Wonderful! (1,004 reviews)
Pleasant staff. Good location to walk to restaurants, shops.

Reviewed on Dec 30, 2025

Graduate by Hilton Annapolis
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
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! (1,885 reviews)
H

Reviewed on Jan 7, 2026

Historic Inns of 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
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
8.8/10 Excellent! (896 reviews)
Very welcoming and room very clean.

Reviewed on Jan 4, 2026

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
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! (1,001 reviews)
Easy

Reviewed on Jan 4, 2026

Crowne Plaza Annapolis by IHG
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
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 helpful ...
8.4/10 Very Good! (1,013 reviews)
We did not eat breakfast at the hotel-it was not included. I only tried to get coffee once and it was full of grounds. Most hotels have coffee and water out all day but there wasn't any available in the lobby in the afternoon or evening.

Reviewed on Jan 9, 2026

Hilton Garden Inn Annapolis Downtown
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
Book a stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,000 reviews)
No hot water for the entire first night. Had plans for the night but could not take shower. Not a good experience. Other than that, everything was fine.

Reviewed on Jan 4, 2026

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
Book a stay at this spa hotel in Annapolis. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (999 reviews)
We were able to get there an hour early and our room was ready and the staff were great!

Reviewed on Jan 3, 2026

The Westin Annapolis
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
Book a stay at this business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9.4/10 Exceptional! (697 reviews)
All of the above and a great view!

Reviewed on Jan 11, 2026

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
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! (975 reviews)
Staff was extremely friendly and helpful. Breakfast was delicious. Hotel was very clean and comfortable. We loved our room. Kitchen very useful as we brought leftovers and were able to heat them up in room and didn't need to go out to restaurant. Very comfortable mattress. All in all an excellent ...

Reviewed on Jan 4, 2026

Sonesta ES Suites Annapolis
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
124 Womack Dr Annapolis MD
  • 14 min drive from Chesapeake Exploration Center
Book a stay at this family-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,000 reviews)
Everything was great about my stay. From checking in to checking out! The front desk staff as well as housekeeping were extremely helpful and kind! I look forward to my next visit!

Reviewed on Jan 4, 2026

Hampton Inn & Suites 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
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,000 reviews)
Good value and close to downtown.

Reviewed on Dec 31, 2025

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.

Find cheap hotels in Chester

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If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $85. 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 1,193 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 $85.

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.