Search for Cheap Deals on
Hotels in Chestertown

Check Last Minute Chestertown Hotel Deals

Tonight May 1 - May 2This weekend May 1 - May 3

Choose from 1090 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! (909 reviews)
Traveling on 301 to New England somewhat off the beaten path Service excellent

Reviewed on Apr 28, 2026

Comfort 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! (80 reviews)
A lovely spot with views of the marina. We went in the offseason, so there were very few hotel guests and the price was extremely reasonable. Memory foam mattresses. Nothing fancy, but it had a small fridge and free coffee from a station in the hall. Note: no elevator, so if mobility is an issue, ...

Reviewed on Apr 23, 2026

The Lodge at Great Oak Landing
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! (1,001 reviews)
Ac was good

Reviewed on Apr 29, 2026

Hampton Inn Baltimore/Glen Burnie
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! (1,843 reviews)
Charming

Reviewed on May 1, 2026

Historic Inns of Annapolis
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! (1,192 reviews)
During our stay, both the hotel lobby and our room had an unpleasant smell. We requested towels from the front desk, and they were never delivered Also , housekeeping never cleaned our room during our stay. The next day, we asked again for towels and washcloths and were told housekeeping would bring ...

Reviewed on May 1, 2026

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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! (1,001 reviews)
Stayed at Pendry Baltimore recently and was disappointed. The cleanliness was poor; bathroom ceiling had cracked paint and the ventilation system appeared moldy. Service at the bar was also lacking, with staff coming off as rude and inattentive. Food quality didn’t help either; the meatballs were ...

Reviewed on Apr 30, 2026

Pendry Baltimore
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! (1,005 reviews)
Very difficult to get on Internet. 😞

Reviewed on May 1, 2026

Best Western Plus Hotel & Conference Center
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)
Good stay

Reviewed on Apr 29, 2026

Hilton Garden Inn Baltimore/White Marsh
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. ...
7.6/10 Good! (1,000 reviews)
Breakfast was mediocre, but staff were working hard to keep buffet line full. TV remote did not work. Staff immediately replaced batteries but it did not work when TV was turned off for the night. Unsuccessful getting it to work in the AM. Check in was easy. Bed was comfortable. Comforter was very ...

Reviewed on Apr 27, 2026

Hampton 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! (1,003 reviews)
Friendly staff. Great breakfast. Nice, clean and welcoming.

Reviewed on May 1, 2026

Hampton Inn Baltimore Bayview Campus
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! (1,000 reviews)
Great location, excellent customer service, quiet, convenient.

Reviewed on Apr 28, 2026

Fairfield Inn & Suites by Marriott White Marsh
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 out of 5
2110 Emmorton Park Rd 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 breakfast and the helpful staff ...
9.4/10 Exceptional! (1,001 reviews)
excellent all around.

Reviewed on May 1, 2026

Hampton Inn & Suites Edgewood/Aberdeen-South
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

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 Chestertown 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 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 1,090 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 $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 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 $85.

How many hotels are there in Chestertown?

With over 1,090 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 $85.

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.