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.

Find my perfect hotel Rooms Check-In Check-Out  
Show Calendar Show Calendar Start My Search >
(select the discounts you qualify for)
Star Rating




Hotel Name

Price Range (USD)
to
Amenities







Set My Filter

Chestertown Hotels/Accommodations

Driftwood Inn : 609 Washington Ave.
+1-800-230-4134Check Rates
609 Washington Ave., Chestertown, MD 21620
  • Low-priced Riverfront hotel
  • Hotel has 3 suites
Comfort Suites
+1-800-997-5148Check Rates
160 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Hotel Reviews
  • 3 star Rural hotel
  • 3 floors in property
Image of Holiday Inn Express & SuitesHoliday Inn Express & Suites
+1-800-997-5149Check Rates
150 Scheeler Rd., Chestertown, MD 21620
  • 4.0/5, Very Good Review Score
  • 3 star Suburban property
  • Free breakfast
Exterior 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 Review Score
  • Three Star Rural property
  • 3 meeting rooms in property
~18.94 Miles from Chestertown
Photo of Best Western Kent Narrows InnBest Western Kent Narrows Inn
+1-800-997-5148Check Rates
3101 Main St., Grasonville, MD 21638
  • 3.5/5, Average Reviews
  • Midscale Resort hotel
  • Fitness / Gym is on-site
~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
  • 3 star Riverfront hotel
  • Check-in: 03:00PM
~19.11 Miles from Chestertown
Photo of Sleep Inn Grasonville Md.Sleep Inn Grasonville Md. in Grasonville
+1-800-230-4134Check Rates
101 V.f.w Ave., Grasonville, MD 21638
  • Inexpensive Resort property
  • Hotel has 59 rooms
~19.69 Miles from Chestertown
Image of Brand New Home2 Suites by Hilton AberdeenBrand New Home2 Suites by Hilton Aberdeen
+1-800-997-5148Check Rates
20 Newton Rd., Aberdeen, MD 21001
  • Affordable Suburban hotel
  • 107 suites in hotel
~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
  • Cheap Downtown hotel
  • Hotel has 4 suites
~20.62 Miles from Chestertown
Wingate by Wyhdham in Belcamp
+1-800-230-4134Check Rates
1326 Policy Dr., Belcamp, MD 21017
  • Midscale Suburban property
  • 3 conference rooms in property
~20.98 Miles from Chestertown
Photo of Sleep Inn & SuitesSleep Inn & Suites : 1807 Edgewood Rd.
+1-800-997-5148Check Rates
1807 Edgewood Rd., Edgewood, MD 21040 Website
  • 3.5/5, Average Recent Reviews
  • Economical Suburban hotel
  • Check-in time: 11:00 am
~21.07 Miles from Chestertown
Motel 6 Edgewood in Edgewood
+1-800-997-5149Check Rates
1709 Edgewood Rd., Edgewood, MD 21040
  • 2.5/5, Poor Latest Reviews
  • Cheap Highway hotel
  • Gym is available on property
~21.11 Miles from Chestertown
Ramada Conference Center
+1-800-230-4134Check Rates
1700 Van Bibber Rd., Edgewood, MD 21040
  • 3.0/5, Average Recent Reviews
  • Economy Suburban hotel
  • 2 floors in property
~21.20 Miles from Chestertown
Candlewood Suites Bel Air in Bel Air
+1-800-997-5148Check Rates
4216 Philadelphia Rd., Bel Air, MD 21015
  • 4.0/5, Very Good Guest Reviews
  • Low-priced Suburban property
  • 3 floors in hotel
~21.20 Miles from Chestertown
Extended Stay America Baltimore Bel Air - Bel Air
+1-800-997-5149Check Rates
1361 James Way, Bel Air, MD 21015
  • 4.0/5, Very Good Reviews
  • Economy hotel
~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
  • Three Star Suburban property
  • 6 suites in property
~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 21040~21.27 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 Hotel Reviews
  • Mid-scale Suburban property
  • 92 rooms in hotel
~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
  • Hotel has 119 suites
~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 Recent Reviews
  • Three Star Rural property
  • 26 suites in property
~21.31 Miles from Chestertown

 [1 - 20 of 50]   


Next: See My Chestertown Hotels with Pricing >