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.

Find my perfect hotel Rooms Check-In Check-Out  
Show Calendar Show Calendar Start My Search >
(select the discounts you qualify for)
Star Rating




Hotel Name

Price Range (USD)
to
Amenities







Set My Filter

Chestertown Hotels, Motels & Accommodations

Driftwood Inn
+1-800-230-4134Check Rates
609 Washington Ave., Chestertown, MD 21620
  • Cheap Riverfront hotel
  • Check in time: 2:00pm
Comfort Suites : 160 Scheeler Rd.
+1-800-997-5148Check Rates
160 Scheeler Rd., Chestertown, MD 21620
Exterior of Holiday Inn Express & SuitesHoliday Inn Express & Suites in Chestertown
+1-800-997-5149Check Rates
150 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Guest Reviews
  • Three Star Suburban hotel
  • 20 suites in hotel
Image 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 Read Reviews
  • Mid-scale Rural property
  • 76 sleeping rooms in hotel
~18.94 Miles from Chestertown
Exterior 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 Reviews
  • Affordable Resort property
  • Fitness + Health Center
~19.10 Miles from Chestertown
Image of Hilton Garden Inn Kent IslandHilton Garden Inn Kent Island : 3206 Main St.
+1-800-997-5149Check Rates
3206 Main St., Grasonville, MD 21638
  • 4.5/5, Very Good Reviews
  • Mid-scale Riverfront property
  • Fitness + Health Center
~19.11 Miles from Chestertown
Photo 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
  • 59 sleeping rooms in hotel
~19.69 Miles from Chestertown
Photo of Brand New Home2 Suites by Hilton AberdeenBrand New Home2 Suites by Hilton Aberdeen - Aberdeen
+1-800-997-5148Check Rates
20 Newton Rd., Aberdeen, MD 21001
  • Three Star Suburban hotel
  • 107 rooms in property
~20.61 Miles from Chestertown
Budget Inn of Aberdeen - Aberdeen
+1-800-997-5149Check Rates
1112 South Philadelphia Blvd., Aberdeen, MD 21001
  • Low Cost hotel
~20.62 Miles from Chestertown
Wingate by Wyhdham in Belcamp
+1-800-230-4134Check Rates
1326 Policy Dr., Belcamp, MD 21017
  • Three Star Suburban hotel
  • Hotel has 3 meeting rooms
~20.98 Miles from Chestertown
Photo of Sleep Inn & SuitesSleep Inn & Suites
+1-800-997-5148Check Rates
1807 Edgewood Rd., Edgewood, MD 21040 Website
  • 3.5/5, Average Reviews
  • Two-star Suburban hotel
  • 16 suites in property
~21.07 Miles from Chestertown
Motel 6 Edgewood in Edgewood
+1-800-997-5149Check Rates
1709 Edgewood Rd., Edgewood, MD 21040
  • 2.5/5, Poor Guest Reviews
  • Cheap Highway hotel
  • Check in time: 3:00PM
~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 Reviews
  • Cheap Suburban hotel
  • 152 rooms in hotel
~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 Guest Reviews
  • Cheap Suburban hotel
  • 95 rooms in hotel
~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 : 2118 Emmorton Park Rd.
+1-800-230-4134Check Rates
2118 Emmorton Park Rd., Edgewood, MD 21040
  • 4.0/5, Very Good Latest Reviews
  • 3-star Suburban hotel
  • 3 floors in property
~21.23 Miles from Chestertown
Image of Comfort Inn & Suites Aberdeen Proving Grounds AreaComfort Inn & Suites Aberdeen Proving Grounds Area - Edgewood
+1-800-997-5148Check Rates
2112a Emmorton Park Rd., Edgewood, MD 21040
  • 4.5/5, Very Good Guest Reviews
  • Low priced Suburban hotel
  • 2 floors 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 Reviews
  • Affordable Suburban hotel
  • Gym / Fitness Center Available
~21.28 Miles from Chestertown
Springhill Suites by Marriott Edgewood Aberdeen in Bel Air
+1-800-230-4134Check Rates
1420 Handlir Dr., Bel Air, MD 21015
  • 4.0/5, Very Good Read Reviews
  • Affordable Highway property
  • 3 floors in property
~21.29 Miles from Chestertown
Hampton Inn in Edgewood
+1-800-997-5148Check Rates
2112 Emmorton Park Rd., Edgewood, MD 21040
  • Low-priced Suburban property
  • 2 floors in property
~21.30 Miles from Chestertown

 [1 - 20 of 50]   


Next: See My Chestertown Hotels with Pricing >