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
  • Economical Riverfront hotel
  • Hotel has 27 rooms
Comfort Suites - Chestertown
+1-800-997-5148Check Rates
160 Scheeler Rd., Chestertown, MD 21620
Exterior of Holiday Inn Express & SuitesHoliday Inn Express & Suites - Chestertown
+1-800-997-5149Check Rates
150 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Recent Reviews
  • Mid-scale Suburban property
  • Hotel has 81 rooms
Image of Holiday Inn Express Kent Island / Annapolis EastHoliday 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 Read Reviews
  • 3-star Rural hotel
  • 3 meeting rooms in property
~18.94 Miles from Chestertown
Exterior of Best Western Kent Narrows InnBest Western Kent Narrows Inn - Grasonville
+1-800-997-5148Check Rates
3101 Main St., Grasonville, MD 21638
  • 3.5/5, Average Latest Reviews
  • Cheap Resort property
  • Check in time: 3:00 PM
~19.10 Miles from Chestertown
Image 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 Reviews
  • Affordable Riverfront hotel
  • Hotel has 5 floors
~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
  • Two star Resort hotel
  • Hotel has 2 suites
~19.69 Miles from Chestertown
Image of Home2 Suites by Hilton AberdeenHome2 Suites by Hilton Aberdeen
+1-800-997-5148Check Rates
20 Newton Rd., Aberdeen, MD 21001
  • Mid-scale Suburban hotel
  • Hotel has an eco-friendly policy See more
~20.61 Miles from Chestertown
Budget Inn of Aberdeen - Aberdeen
+1-800-997-5149Check Rates
1112 South Philadelphia Blvd., Aberdeen, MD 21001
  • Low Cost Downtown hotel
  • Check-in: 12.00
~20.62 Miles from Chestertown
Wingate by Wyhdham in Belcamp
+1-800-230-4134Check Rates
1326 Policy Dr., Belcamp, MD 21017
  • Affordable Suburban property
  • 7 suites in hotel
~20.98 Miles from Chestertown
Photo of Sleep Inn & SuitesSleep Inn & Suites - Edgewood
+1-800-997-5148Check Rates
1807 Edgewood Rd., Edgewood, MD 21040
  • 3.5/5, Average Hotel Reviews
  • Low priced Suburban hotel
  • 84 rooms 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
  • Two star Highway property
  • 22 suites in hotel
~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 Latest Reviews
  • Economical Suburban hotel
  • 4 conference rooms in property
~21.20 Miles from Chestertown
Photo of Candlewood Suites Bel AirCandlewood Suites Bel Air - Bel Air
+1-800-997-5148Check Rates
4216 Philadelphia Rd., Bel Air, MD 21015 Website
  • 4.0/5, Very Good Read Reviews
  • 2-star Suburban hotel
  • Fitness / Gym is 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 21015~21.23 Miles from Chestertown
Holiday Inn Express in Edgewood
+1-800-230-4134Check Rates
2118 Emmorton Park Rd., Edgewood, MD 21040
  • 4.0/5, Very Good Review Score
  • Midscale Suburban hotel
  • Gym / Fitness Center Available
~21.23 Miles from Chestertown
Exterior of Comfort Inn & Suites Aberdeen Proving Grounds AreaComfort Inn & Suites Aberdeen Proving Grounds Area
+1-800-997-5148Check Rates
2112a Emmorton Park Rd., Edgewood, MD 21040
  • 4.5/5, Very Good Reviews
  • Two-star Suburban property
  • 20 suites in property
~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 Reviews
  • Midscale Suburban hotel
  • Check-in time: 3:00pm
~21.28 Miles from Chestertown
Springhill Suites by Marriott Edgewood Aberdeen - Bel Air
+1-800-230-4134Check Rates
1420 Handlir Dr., Bel Air, MD 21015
  • 4.0/5, Very Good Guest Reviews
  • Three Star Highway hotel
  • Free breakfast available
~21.29 Miles from Chestertown
Country Inn & Suites Bel Air E. (Aberdeen) at I 95
+1-800-997-5148Check Rates
1435 Handlir Dr., Bel Air, MD 21015
  • 4.5/5, Very Good Review Score
  • Midscale Rural hotel
  • Hotel has 3 floors
~21.31 Miles from Chestertown

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