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 : 609 Washington Ave.
+1-800-230-4134Check Rates
609 Washington Ave., Chestertown, MD 21620
  • 2-star Riverfront property
  • Check-in time: 2:00pm
Comfort Suites : 160 Scheeler Rd.
+1-800-997-5148Check Rates
160 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Read Reviews
  • 3-star Rural property
  • Hotel has 53 rooms
Image 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 Recent Reviews
  • Affordable Suburban property
  • 20 suites in hotel
Image of Holiday Inn Express Kent Island / Annapolis East Holiday Inn Express Kent Island / Annapolis East : 1020 Kent Narrows Rd.
+1-800-230-4134Check Rates
1020 Kent Narrows Rd., Grasonville, MD 21638
  • 4.0/5, Very Good Review Score
  • Three Star Rural property
  • Hotel has 3 meeting rooms
~18.94 Miles from Chestertown
Photo of Best Western Kent Narrows Inn Best Western Kent Narrows Inn - Grasonville
+1-800-997-5148Check Rates
3101 Main St., Grasonville, MD 21638
  • 3.5/5, Average Reviews
  • Mid-scale Resort property
  • Check in: 3:00 PM
~19.10 Miles from Chestertown
Image 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 Latest Reviews
  • Three Star Riverfront hotel
  • Access to gym on-site
~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
  • Economical Resort hotel
  • Check-in: 3:00 PM
~19.69 Miles from Chestertown
Photo of Brand New Home2 Suites by Hilton Aberdeen Brand New Home2 Suites by Hilton Aberdeen : 20 Newton Rd.
+1-800-997-5148Check Rates
20 Newton Rd., Aberdeen, MD 21001
  • 3-star Suburban property
  • 107 sleeping rooms in hotel
~20.61 Miles from Chestertown
Budget Inn of Aberdeen
+1-800-997-5149Check Rates
1112 South Philadelphia Blvd., Aberdeen, MD 21001
  • Low priced hotel
~20.62 Miles from Chestertown
Wingate by Wyndham Belcamp Aberdeen in Belcamp
+1-800-230-4134Check Rates
1326 Policy Dr., Belcamp, MD 21017
  • 4.0/5, Very Good Review Score
  • 3-star Suburban hotel
  • Hotel has 7 suites
~20.97 Miles from Chestertown
Photo of Sleep Inn & Suites Sleep Inn & Suites - Edgewood
+1-800-997-5148Check Rates
1807 Edgewood Rd., Edgewood, MD 21040 Website
  • 3.5/5, Average Reviews
  • Two-star Suburban hotel
  • 16 suites in hotel
~21.07 Miles from Chestertown
Motel 6 Edgewood
+1-800-997-5149Check Rates
1709 Edgewood Rd., Edgewood, MD 21040
  • 2.5/5, Poor Guest Reviews
  • 2-star Highway hotel
  • Check-in: 3:00PM
~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 Hotel Reviews
  • Economy Suburban hotel
  • Fitness center on property
~21.20 Miles from Chestertown
Candlewood Suites Bel Air - Bel Air
+1-800-997-5148Check Rates
4216 Philadelphia Rd., Bel Air, MD 21015
  • 4.0/5, Very Good Reviews
  • Two star Suburban property
  • Hotel has a green policy Learn more
~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 ~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 Recent Reviews
  • Affordable Suburban property
  • Check-in time: 3:00 pm
~21.23 Miles from Chestertown
Exterior 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 Hotel Reviews
  • Low Cost Suburban hotel
  • Fitness + Health Center
~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
  • 3 star Suburban hotel
  • 92 rooms in property
~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
  • 3.5/5, Average Review Score
  • Three Star Highway hotel
  • Check in: 3:00pm
~21.29 Miles from Chestertown
Hampton Inn
+1-800-997-5148Check Rates
2112 Emmorton Park Rd., Edgewood, MD 21040
  • Inexpensive Suburban hotel
  • Free breakfast available
~21.30 Miles from Chestertown

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