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
  • Inexpensive Riverfront property
  • Hotel has 27 rooms
Comfort Suites
+1-800-997-5148Check Rates
160 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Guest Reviews
  • Mid-scale Rural hotel
  • 53 sleeping rooms in hotel
Photo of Holiday Inn Express & SuitesHoliday Inn Express & Suites
+1-800-997-5149Check Rates
150 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Read Reviews
  • Mid-scale Suburban hotel
  • 81 sleeping rooms 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 Recent Reviews
  • 3 star Rural property
  • 3 conference rooms in property
~18.94 Miles from Chestertown
Image of Best Western Kent Narrows InnBest Western Kent Narrows Inn - Grasonville
+1-800-997-5148Check Rates
3101 Main St., Grasonville, MD 21638~19.10 Miles from Chestertown
Photo 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
  • 3-star Riverfront property
  • 90 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
  • Two-star Resort property
  • 2 suites in property
~19.69 Miles from Chestertown
Photo of Brand New Home2 Suites by Hilton AberdeenBrand New Home2 Suites by Hilton Aberdeen in Aberdeen
+1-800-997-5148Check Rates
20 Newton Rd., Aberdeen, MD 21001
  • 3 star Suburban property
  • Hotel has 107 rooms
~20.61 Miles from Chestertown
Wingate by Wyndham Belcamp Aberdeen
+1-800-997-5149Check Rates
1326 Policy Dr., Belcamp, MD 21017
  • 4.0/5, Very Good Hotel Reviews
  • 3 star Suburban property
  • 3 conference rooms in property
~20.97 Miles from Chestertown
Photo of Sleep Inn & SuitesSleep Inn & Suites in Edgewood
+1-800-230-4134Check Rates
1807 Edgewood Rd., Edgewood, MD 21040 Website
  • 3.5/5, Average Guest Reviews
  • Economy Suburban property
  • 3 floors in property
~21.07 Miles from Chestertown
Motel 6 Edgewood
+1-800-997-5148Check Rates
1709 Edgewood Rd., Edgewood, MD 21040
  • 2.5/5, Poor Review Score
  • Cheap Highway hotel
  • Check-in time: 3:00PM
~21.11 Miles from Chestertown
Ramada Conference Center in Edgewood
+1-800-997-5149Check Rates
1700 Van Bibber Rd., Edgewood, MD 21040
  • 3.0/5, Average Reviews
  • Inexpensive Suburban property
  • Access to gym on-site
~21.20 Miles from Chestertown
Candlewood Suites Bel Air
+1-800-230-4134Check Rates
4216 Philadelphia Rd., Bel Air, MD 21015
  • 4.0/5, Very Good Guest Reviews
  • Cheap Suburban property
  • 95 suites in property
~21.20 Miles from Chestertown
Extended Stay America Baltimore Bel Air
+1-800-997-5148Check Rates
1361 James Way, Bel Air, MD 21015~21.23 Miles from Chestertown
Holiday Inn Express
+1-800-997-5149Check Rates
2118 Emmorton Park Rd., Edgewood, MD 21040
  • 4.0/5, Very Good Guest Reviews
  • Mid-scale Suburban hotel
  • Free comp. breakfast
~21.23 Miles from Chestertown
Image of Comfort Inn & Suites Aberdeen Proving Grounds AreaComfort Inn & Suites Aberdeen Proving Grounds Area
+1-800-230-4134Check Rates
2112a Emmorton Park Rd., Edgewood, MD 21040
  • 4.5/5, Very Good Review Score
  • Inexpensive Suburban property
  • Access to gym on-site
~21.27 Miles from Chestertown
Homewood Suites by Hilton - Bel Air
+1-800-997-5148Check Rates
4170 Philadelphia Rd., Bel Air, MD 21015
  • 4.5/5, Very Good Review Score
  • Affordable Suburban hotel
  • 5 floors in property
~21.28 Miles from Chestertown
Springhill Suites by Marriott Edgewood Aberdeen
+1-800-997-5149Check Rates
1420 Handlir Dr., Bel Air, MD 21015
  • 3.5/5, Average Hotel Reviews
  • Affordable Highway hotel
  • Access to gym on-site
~21.29 Miles from Chestertown
Hampton Inn in Edgewood
+1-800-230-4134Check Rates
2112 Emmorton Park Rd., Edgewood, MD 21040
  • Two-star Suburban hotel
  • 40 suites in hotel
~21.30 Miles from Chestertown
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 in Bel Air
+1-800-997-5148Check Rates
1435 Handlir Dr., Bel Air, MD 21015
  • 4.5/5, Very Good Review Score
  • 3 star Rural hotel
  • Free breakfast
~21.31 Miles from Chestertown

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