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
  • Two star Riverfront hotel
  • Check-in time: 2:00pm
Comfort Suites - Chestertown
+1-800-997-5148Check Rates
160 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Guest Reviews
  • Mid-scale Rural hotel
  • 53 rooms in property
Exterior 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 Read Reviews
  • 3-star Suburban property
  • 20 suites in hotel
Photo of Holiday Inn Express Kent Island / Annapolis East Holiday Inn Express Kent Island / Annapolis East - Grasonville
+1-800-230-4134Check Rates
1020 Kent Narrows Rd., Grasonville, MD 21638
  • 4.0/5, Very Good Review Score
  • 3 star Rural hotel
  • 3 conference rooms in property
~18.94 Miles from Chestertown
Image 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
  • Affordable Resort property
  • 92 sleeping rooms in hotel
~19.10 Miles from Chestertown
Image of Hilton Garden Inn Kent Island Hilton Garden Inn Kent Island : 3206 Main St.
+1-800-997-5149Check Rates
3206 Main St., Grasonville, MD 21638
  • 4.5/5, Very Good Reviews
  • 3 star Riverfront hotel
  • Hotel has 4 meeting rooms
~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
  • Cheap Resort property
  • Check-in time: 3:00 PM
~19.69 Miles from Chestertown
Photo of Home2 Suites by Hilton Aberdeen Home2 Suites by Hilton Aberdeen - Aberdeen
+1-800-997-5148Check Rates
20 Newton Rd., Aberdeen, MD 21001
  • Midscale Suburban property
  • Hotel has 107 suites
~20.61 Miles from Chestertown
Budget Inn of Aberdeen
+1-800-997-5149Check Rates
1112 South Philadelphia Blvd., Aberdeen, MD 21001
  • Two star Downtown property
  • 4 suites in hotel
~20.62 Miles from Chestertown
Wingate by Wyhdham in Belcamp
+1-800-230-4134Check Rates
1326 Policy Dr., Belcamp, MD 21017
  • 3-star Suburban hotel
  • 7 suites in hotel
~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 Recent Reviews
  • Two star Suburban property
  • Gym is available on property
~21.07 Miles from Chestertown
Motel 6 Edgewood
+1-800-997-5149Check Rates
1709 Edgewood Rd., Edgewood, MD 21040
  • 2.5/5, Poor Hotel Reviews
  • Low Cost Highway property
  • Check in time: 3:00PM
~21.11 Miles from Chestertown
Candlewood Suites Bel Air in Bel Air
+1-800-230-4134Check Rates
4216 Philadelphia Rd., Bel Air, MD 21015
  • 4.0/5, Very Good Read Reviews
  • Low priced Suburban hotel
  • 3 floors in hotel
~21.20 Miles from Chestertown
Ramada Conference Center - Edgewood
+1-800-997-5148Check Rates
1700 Van Bibber Rd., Edgewood, MD 21040
  • 3.0/5, Average Review Score
  • Low-priced Suburban hotel
  • 152 rooms in property
~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 - Edgewood
+1-800-230-4134Check Rates
2118 Emmorton Park Rd., Edgewood, MD 21040
  • 4.0/5, Very Good Recent Reviews
  • 3-star Suburban hotel
  • Gym / Fitness Center Available
~21.23 Miles from Chestertown
Exterior of Comfort Inn & Suites Aberdeen Proving Grounds Area Comfort Inn & Suites Aberdeen Proving Grounds Area : 2112a Emmorton Park Rd.
+1-800-997-5148Check Rates
2112a Emmorton Park Rd., Edgewood, MD 21040
  • 4.5/5, Very Good Hotel Reviews
  • Cheap Suburban hotel
  • 2 floors in hotel
~21.27 Miles from Chestertown
Homewood Suites by Hilton in Bel Air
+1-800-997-5149Check Rates
4170 Philadelphia Rd., Bel Air, MD 21015
  • 4.5/5, Very Good Review Score
  • Mid-scale Suburban property
  • 92 sleeping rooms in hotel
~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
  • Affordable Highway property
  • 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 Latest Reviews
  • 3 star Rural property
  • Fitness / Gym is on-site
~21.31 Miles from Chestertown

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