Chestertown Maryland Hotels & Motels

Find hotels in Chestertown using the list and search tools below. Find discounted hotel accommodations in or close to Chestertown, MD for your upcoming individual or group travel. We list the best Chestertown, Maryland motel and hotel rooms. Browse the Chestertown area hotels to find the perfect lodging! Please use the provided map of the Chestertown hotels. Booking 5+ Rooms? Find Chestertown Group Hotel Discounts

The Chestertown center point is about 21 miles from Ripken Museum and 21 miles from Aberdeen Amtrak Station.

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Chestertown Hotels/Accommodations

Driftwood Inn in Chestertown
+1-800-230-4134Check Rates
609 Washington Ave., Chestertown, MD 21620
  • Low-priced Riverfront hotel
  • Check-in time: 2:00pm
Comfort Suites in Chestertown
+1-800-997-5148Check Rates
160 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Recent Reviews
  • Mid-scale Rural property
  • 3 floors in property
Photo of Holiday Inn Express & SuitesHoliday Inn Express & Suites
+1-800-997-5149Check Rates
150 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Review Score
  • Mid-scale Suburban property
  • 20 suites in hotel
Photo of Holiday Inn Express Kent Island / Annapolis EastHoliday Inn Express Kent Island / Annapolis East
+1-800-230-4134Check Rates
1020 Kent Narrows Rd., Grasonville, MD 21638
  • 4.0/5, Very Good Hotel Reviews
  • Three Star Rural hotel
  • 3 meeting rooms in hotel
~18.94 Miles from Chestertown
Image of Best Western Kent Narrows InnBest Western Kent Narrows Inn
+1-800-997-5148Check Rates
3101 Main St., Grasonville, MD 21638
  • 3.5/5, Average Read Reviews
  • Midscale Resort property
  • 92 sleeping rooms in hotel
~19.10 Miles from Chestertown
Photo of Hilton Garden Inn Kent IslandHilton Garden Inn Kent Island - Grasonville
+1-800-997-5149Check Rates
3206 Main St., Grasonville, MD 21638
  • 4.5/5, Very Good Latest Reviews
  • 3-star Riverfront property
  • 5 floors in property
~19.11 Miles from Chestertown
Exterior of Sleep Inn Grasonville Md.Sleep Inn Grasonville Md.
+1-800-230-4134Check Rates
101 V.f.w Ave., Grasonville, MD 21638
  • Cheap Resort hotel
  • 2 floors in property
~19.69 Miles from Chestertown
Image of Brand New Home2 Suites by Hilton AberdeenBrand New Home2 Suites by Hilton Aberdeen
+1-800-997-5148Check Rates
20 Newton Rd., Aberdeen, MD 21001
  • Three Star Suburban hotel
  • Free complimentary breakfast
~20.61 Miles from Chestertown
Budget Inn of Aberdeen in Aberdeen
+1-800-997-5149Check Rates
1112 South Philadelphia Blvd., Aberdeen, MD 21001
  • Two star property
~20.62 Miles from Chestertown
Wingate by Wyhdham in Belcamp
+1-800-230-4134Check Rates
1326 Policy Dr., Belcamp, MD 21017
  • Three Star Suburban property
  • Fitness + Health Center
~20.98 Miles from Chestertown
Image of Sleep Inn & SuitesSleep Inn & Suites - Edgewood
+1-800-997-5148Check Rates
1807 Edgewood Rd., Edgewood, MD 21040 Website
  • 3.5/5, Average Read Reviews
  • 2-star Suburban hotel
  • 3 floors in property
~21.07 Miles from Chestertown
Motel 6 Edgewood : 1709 Edgewood Rd.
+1-800-997-5149Check Rates
1709 Edgewood Rd., Edgewood, MD 21040
  • 2.5/5, Poor Hotel Reviews
  • Economy Highway property
  • Hotel has 2 floors
~21.11 Miles from Chestertown
Ramada Conference Center in Edgewood
+1-800-230-4134Check Rates
1700 Van Bibber Rd., Edgewood, MD 21040
  • 3.0/5, Average Hotel Reviews
  • Economical Suburban property
  • Fitness / Gym is on-site
~21.20 Miles from Chestertown
Candlewood Suites Bel Air
+1-800-997-5148Check Rates
4216 Philadelphia Rd., Bel Air, MD 21015
  • 4.0/5, Very Good Latest Reviews
  • Cheap Suburban hotel
  • 3 floors in property
~21.20 Miles from Chestertown
Extended Stay America Baltimore Bel Air
+1-800-997-5149Check Rates
1361 James Way, Bel Air, MD 21015~21.23 Miles from Chestertown
Holiday Inn Express
+1-800-230-4134Check Rates
2118 Emmorton Park Rd., Edgewood, MD 21040
  • 4.0/5, Very Good Review Score
  • Mid-scale Suburban property
  • Fitness center on property
~21.23 Miles from Chestertown
Image of Comfort Inn & Suites Aberdeen Proving Grounds AreaComfort Inn & Suites Aberdeen Proving Grounds Area : 2112a Emmorton Park Rd.
+1-800-997-5148Check Rates
2112a Emmorton Park Rd., Edgewood, MD 21040
  • 4.5/5, Very Good Guest Reviews
  • Low-priced Suburban hotel
  • 40 suites in hotel
~21.27 Miles from Chestertown
Homewood Suites by Hilton
+1-800-997-5149Check Rates
4170 Philadelphia Rd., Bel Air, MD 21015
  • 4.5/5, Very Good Read Reviews
  • Affordable Suburban property
  • Free comp. breakfast
~21.28 Miles from Chestertown
Springhill Suites by Marriott Edgewood Aberdeen
+1-800-230-4134Check Rates
1420 Handlir Dr., Bel Air, MD 21015
  • 4.0/5, Very Good Read Reviews
  • Mid-scale Highway property
  • 3 floors in property
~21.29 Miles from Chestertown
Hampton Inn - Edgewood
+1-800-997-5148Check Rates
2112 Emmorton Park Rd., Edgewood, MD 21040
  • Two-star Suburban hotel
  • Fitness center on property
~21.30 Miles from Chestertown

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