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, Motels & Accommodations

Driftwood Inn in Chestertown
+1-800-230-4134Check Rates
609 Washington Ave., Chestertown, MD 21620
  • Two star Riverfront hotel
  • 27 rooms in hotel
Comfort Suites
+1-800-997-5148Check Rates
160 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Review Score
  • Midscale Rural hotel
  • 3 floors in hotel
Photo of Holiday Inn Express & Suites Holiday Inn Express & Suites
+1-800-997-5149Check Rates
150 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Reviews
  • Affordable Suburban property
  • Hotel has 3 floors
Exterior of Holiday Inn Express Kent Island / Annapolis East Holiday 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
  • 3 star Rural property
  • Free complimentary breakfast
~18.94 Miles from Chestertown
Photo of Best Western Kent Narrows Inn Best Western Kent Narrows Inn
+1-800-997-5148Check Rates
3101 Main St., Grasonville, MD 21638
  • 3.5/5, Average Reviews
  • Three Star Resort hotel
  • Check-in time: 3:00 PM
~19.10 Miles from Chestertown
Exterior of Hilton Garden Inn Kent Island Hilton Garden Inn Kent Island in Grasonville
+1-800-997-5149Check Rates
3206 Main St., Grasonville, MD 21638
  • 4.5/5, Very Good Recent Reviews
  • 3 star Riverfront property
  • 90 sleeping rooms in hotel
~19.11 Miles from Chestertown
Image of Sleep Inn Grasonville Md. Sleep Inn Grasonville Md.
+1-800-230-4134Check Rates
101 V.f.w Ave., Grasonville, MD 21638
  • Economical Resort hotel
  • Hotel has 2 floors
~19.69 Miles from Chestertown
Exterior of Home2 Suites by Hilton Aberdeen Home2 Suites by Hilton Aberdeen
+1-800-997-5148Check Rates
20 Newton Rd., Aberdeen, MD 21001
  • Affordable Suburban hotel
  • Hotel has 107 suites
~20.61 Miles from Chestertown
Budget Inn of Aberdeen : 1112 South Philadelphia Blvd.
+1-800-997-5149Check Rates
1112 South Philadelphia Blvd., Aberdeen, MD 21001
  • Low Cost Downtown hotel
  • Hotel has 4 suites
~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
  • 107 rooms in hotel
~20.98 Miles from Chestertown
Exterior of Sleep Inn & Suites Sleep Inn & Suites
+1-800-997-5148Check Rates
1807 Edgewood Rd., Edgewood, MD 21040 Website
  • 3.5/5, Average Read Reviews
  • 2 star Suburban hotel
  • Check-in: 11:00 am
~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 Review Score
  • Economical Highway hotel
  • 22 suites in property
~21.11 Miles from Chestertown
Ramada Conference Center - Edgewood
+1-800-230-4134Check Rates
1700 Van Bibber Rd., Edgewood, MD 21040
  • 3.0/5, Average Reviews
  • Economical Suburban property
  • Fitness + Health Center
~21.20 Miles from Chestertown
Photo of Candlewood Suites Bel Air Candlewood Suites Bel Air - Bel Air
+1-800-997-5148Check Rates
4216 Philadelphia Rd., Bel Air, MD 21015 Website
  • 4.0/5, Very Good Reviews
  • 2-star Suburban property
  • Access to gym on-site
~21.20 Miles from Chestertown
Extended Stay America Baltimore Bel Air : 1361 James Way
+1-800-997-5149Check Rates
1361 James Way, Bel Air, MD 21015
  • 3.5/5, Average Reviews
  • Low Cost hotel
~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 Read Reviews
  • Midscale Suburban property
  • 6 suites in property
~21.23 Miles from Chestertown
Photo of Comfort Inn & Suites Aberdeen Proving Grounds Area Comfort Inn & Suites Aberdeen Proving Grounds Area
+1-800-997-5148Check Rates
2112a Emmorton Park Rd., Edgewood, MD 21040
  • 4.5/5, Very Good Review Score
  • Inexpensive Suburban property
  • Complimentary breakfast is offered
~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 Latest Reviews
  • Three Star Suburban property
  • 5 floors in hotel
~21.28 Miles from Chestertown
Springhill Suites by Marriott Edgewood Aberdeen : 1420 Handlir Dr.
+1-800-230-4134Check Rates
1420 Handlir Dr., Bel Air, MD 21015
  • 4.0/5, Very Good Recent Reviews
  • Mid-scale Highway hotel
  • 3 floors in hotel
~21.29 Miles from Chestertown
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 - Bel Air
+1-800-997-5148Check Rates
1435 Handlir Dr., Bel Air, MD 21015
  • 4.5/5, Very Good Hotel Reviews
  • Three Star Rural property
  • Check in time: 3pm
~21.31 Miles from Chestertown

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