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Hotels in Chestertown

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Choose from 1095 Chestertown Hotel Deals

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
  • 14 min walk from Washington College
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (913 reviews)
"I called the central reservation desk to extend my stay at 08000 the morning of check-in. They verified the reservation under the current ID was extended. When I confirmed this with the front desk, she said they were no rooms available. There was no discussion and she and the next clerk gave no explanation. ..."

Reviewed on May 19, 2026

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
  • 13 min walk from Washington College
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.2/10 Good! (442 reviews)
"This hotel is in need of repair. The pull out sofa had more rips and tears than what should ever be seen. Way over priced for what you get"

Reviewed on May 19, 2026

Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
  • 8 min drive from Washington College
Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
8/10 Very Good! (82 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again"

Reviewed on May 18, 2026

The Lodge at Great Oak Landing
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
  • 41 min drive from Washington College
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 ...
9/10 Wonderful! (1,837 reviews)
"This was a beautiful historic hotel directly across from the state capitol building. We had excellent service and the valet parking was fast and friendly. Highly recommend this place!"

Reviewed on May 22, 2026

Historic Inns of Annapolis
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
  • 7 min drive from Washington College
Book a stay at this business-friendly hotel in Glen Burnie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,002 reviews)
"Old room, carpet needs some tlc. Plus stood 2 nights and never received housekeeping service."

Reviewed on May 22, 2026

Hampton Inn Baltimore/Glen Burnie
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5
4 Philadelphia Ct Rosedale MD
  • 20 min drive from Washington College
Book a stay at this business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,202 reviews)
"The hotel itself was very acceptable and had a good breakfast. The room was good. The area surrounding the hotel did not feel very safe."

Reviewed on May 21, 2026

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
  • 10 min drive from Washington College
Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,002 reviews)
"Good"

Reviewed on May 20, 2026

Best Western Plus Hotel & Conference Center
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
  • 10 min drive from Washington College
Book a stay at this luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,002 reviews)
"Great room"

Reviewed on May 21, 2026

Pendry Baltimore
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
  • 26 min drive from Washington College
Book a stay at this family-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.8/10 Good! (1,000 reviews)
"Great stay will return"

Reviewed on May 18, 2026

Hilton Garden Inn Baltimore/White Marsh
Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

3.5 out of 5
6571 Eastern Avenue Baltimore MD
  • 11 min drive from Washington College
Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,001 reviews)
"This hotel was very clean and the staff was very helpful. We stayed her on 2 ocassions and will be returning"

Reviewed on May 20, 2026

Hampton Inn Baltimore Bayview Campus
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

2.5 out of 5
8225 Town Center Drive Baltimore MD
  • 25 min drive from Washington College
Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
7.8/10 Good! (1,002 reviews)
"Carpet was worn in my room."

Reviewed on May 21, 2026

Hampton Inn Baltimore/White Marsh
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

3 out of 5
8477 Cordon Way Baltimore MD
  • 26 min drive from Washington College
Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,001 reviews)
"It was an average hotel. It could use some updates such as a higher toilet. Also breakfast eggs were cold and there were no diabetic choices such as sugar free syrup at breakfast . Staff was nice . I’d stay there again if I can’t find another hotel with a better rating."

Reviewed on May 21, 2026

Fairfield Inn & Suites by Marriott White Marsh
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 Chestertown

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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 Chestertown’s 1,095 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 $80. 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 Chestertown hotel deals at the last minute.

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Frequently Asked Questions About Chestertown hotels

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

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How many hotels are there in Chestertown?

With over 1,095 hotels in Chestertown, 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 $80.

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Finding a cheap car rental deal in Chestertown is as easy as scoring cheap hotels in Chestertown. 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.