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
+1-800-230-4134Check Rates
609 Washington Ave., Chestertown, MD 21620
  • Low-priced Riverfront property
  • 27 sleeping rooms in hotel
Comfort Suites - Chestertown
+1-800-997-5148Check Rates
160 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Review Score
  • Affordable Rural hotel
  • Free breakfast available
Photo of Holiday Inn Express & Suites Holiday Inn Express & Suites in Chestertown
+1-800-997-5149Check Rates
150 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Recent Reviews
  • 3 star Suburban property
  • 3 floors in hotel
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
  • Midscale Rural hotel
  • Free breakfast
~18.94 Miles from Chestertown
Image of Best Western Kent Narrows Inn Best Western Kent Narrows Inn in Grasonville
+1-800-997-5148Check Rates
3101 Main St., Grasonville, MD 21638 ~19.10 Miles from Chestertown
Photo of Hilton Garden Inn Kent Island Hilton Garden Inn Kent Island - Grasonville
+1-800-997-5149Check Rates
3206 Main St., Grasonville, MD 21638
  • 4.5/5, Very Good Review Score
  • Affordable Riverfront hotel
  • Hotel has 90 rooms
~19.11 Miles from Chestertown
Photo of Sleep Inn Grasonville Md. Sleep Inn Grasonville Md. - Grasonville
+1-800-230-4134Check Rates
101 V.f.w Ave., Grasonville, MD 21638
  • Low-priced Resort hotel
  • Check in: 3:00 PM
~19.69 Miles from Chestertown
Exterior of Brand New Home2 Suites by Hilton Aberdeen Brand New Home2 Suites by Hilton Aberdeen
+1-800-997-5148Check Rates
20 Newton Rd., Aberdeen, MD 21001
  • 3 star Suburban hotel
  • Fitness / Gym is on-site
~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
  • Check-in time: 12.00
~20.62 Miles from Chestertown
Wingate by Wyhdham - Belcamp
+1-800-230-4134Check Rates
1326 Policy Dr., Belcamp, MD 21017
  • Three Star Suburban property
  • Access to gym on-site
~20.98 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 Latest Reviews
  • Low Cost Suburban property
  • Hotel has 3 floors
~21.07 Miles from Chestertown
Motel 6 Edgewood
+1-800-997-5149Check Rates
1709 Edgewood Rd., Edgewood, MD 21040
  • 2.5/5, Poor Read Reviews
  • Cheap Highway property
  • 22 suites in hotel
~21.11 Miles from Chestertown
Ramada Conference Center : 1700 Van Bibber Rd.
+1-800-230-4134Check Rates
1700 Van Bibber Rd., Edgewood, MD 21040
  • 3.0/5, Average Reviews
  • Inexpensive Suburban hotel
  • 3 suites in property
~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 Read Reviews
  • Low Cost Suburban property
  • Hotel has 95 rooms
~21.20 Miles from Chestertown
Extended Stay America Baltimore Bel Air
+1-800-997-5149Check Rates
1361 James Way, Bel Air, MD 21015
  • 4.0/5, Very Good Reviews
  • 2-star property
~21.23 Miles from Chestertown
Holiday Inn Express - Edgewood
+1-800-230-4134Check Rates
2118 Emmorton Park Rd., Edgewood, MD 21040
  • 4.0/5, Very Good Review Score
  • Midscale Suburban property
  • 6 suites in hotel
~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 Review Score
  • Low Cost Suburban hotel
  • Fitness + Health Center
~21.27 Miles from Chestertown
Homewood Suites by Hilton : 4170 Philadelphia Rd.
+1-800-997-5149Check Rates
4170 Philadelphia Rd., Bel Air, MD 21015
  • 4.5/5, Very Good Recent Reviews
  • Three Star Suburban hotel
  • Check in: 3:00pm
~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 Latest Reviews
  • Affordable Highway property
  • 119 sleeping rooms 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 Guest Reviews
  • Mid-scale Rural hotel
  • Hotel has 26 suites
~21.31 Miles from Chestertown

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