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Hotels in Chestertown

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Choose from 1086 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 ...
8.4/10 Very Good! (857 reviews)
Excellent hotel. Will stay there anytime I travel to the area.

Reviewed on Nov 26, 2025

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! (418 reviews)
room was clean but the shower curtain was in tatters. multiple rings torn off

Reviewed on Nov 20, 2025

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 ...
7.8/10 Good! (76 reviews)
Beautiful view

Reviewed on Nov 8, 2025

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 ...
8.8/10 Excellent! (1,915 reviews)
Upon entering the entire stay was a 10. The valet, seperate, were very courteous. The front desk staff were friendly and extremely helpful. The hotel was decorated for Christmas and was very festive. The room was clean and very roomy. The location could not have been better, directly across from ...

Reviewed on Dec 3, 2025

Historic Inns of Annapolis
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 ...
9.2/10 Wonderful! (1,006 reviews)
Exceptionally thoughtful staff, amazing shower + tub, super clean room and peaceful. :)

Reviewed on Nov 29, 2025

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! (1,014 reviews)
The staff was so friendly, from check in, security, kitchen staff and all. The room was very clean. Breakfast was great! Mrs Cindy was so nice and you can tell she enjoys her job.

Reviewed on Dec 2, 2025

Hilton Garden Inn Baltimore/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! (1,003 reviews)
Amazing staff. Clean room.

Reviewed on Nov 27, 2025

Best Western Plus Hotel & Conference Center
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 ...
8.8/10 Excellent! (1,012 reviews)
YES

Reviewed on Nov 28, 2025

Hampton Inn Baltimore Bayview Campus
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 out of 5
2112a Emmorton Park Road Edgewood MD
  • 39 min drive from Washington College
Book a stay at this business-friendly hotel in Edgewood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,028 reviews)
Was very happy

Reviewed on Nov 29, 2025

Quality Inn & Suites Bel Air I-95 Exit 77A
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 ...
8/10 Very Good! (1,004 reviews)
Room was spotless, beds were very comfortable and breakfast was good

Reviewed on Nov 10, 2025

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! (1,077 reviews)
all was good. I was very pleased.

Reviewed on Nov 26, 2025

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row

3 out of 5
1803 Porter Street Baltimore MD
  • 8 min drive from Washington College
Book a stay at this business-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9/10 Wonderful! (698 reviews)
The staff was wonderful.

Reviewed on Nov 28, 2025

Courtyard by Marriott Baltimore Downtown/McHenry Row
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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For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chestertown.

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 1,086 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 $69. 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.

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 Chestertown. No matter your reason for visiting Chestertown, 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 Chestertown 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 Chestertown for as low as $69.

How many hotels are there in Chestertown?

With over 1,086 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 $69.

How to find cheap car rentals in Chestertown?

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.