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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 south of Ripken Museum and 21 miles south of Aberdeen Amtrak Station.

Chestertown Hotels/Accommodations

Comfort Suites in Chestertown
+1-888-690-5281
160 Scheeler Rd., Chestertown, MD 21620
  • Mid-scale Rural hotel
  • 3 floors in hotel
From$75
Very Good 4.0 /5Reviews Call
Holiday Inn Express & Suites Chestertown Md 150 Scheeler Rd., Chestertown, MD 21620
  • Midscale Suburban property
  • Fitness + Health Center
From$115
Very Good 4.0 /5Guest Reviews Call
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • Four star Rural hotel
  • 13 rooms in property
Holiday Inn Express Kent Island / Annapolis East : 1020 Kent Narrows Rd.
+1-888-690-5247
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Mid-scale Rural hotel
  • 3 floors in property
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Inexpensive Resort hotel
  • Check in: 3:00 PM
Hilton Garden Inn Kent Island in Grasonville 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • 3 star Riverfront hotel
  • 4 meeting rooms in property
From$132
Very Good 4.5 /5Hotel Reviews Call
Sleep Inn Grasonville Md. in Grasonville
+1-800-997-5149
101 V.f.w Ave., Grasonville, MD 21638 ~19.69 miles south of Chestertown
  • Cheap Resort hotel
  • Check-in time: 3:00 PM
From$75
Very Good 4.0 /5Read Reviews Call
Home2 Suites by Hilton Aberdeen in Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Mid-scale Suburban property
  • Fitness center on property
From$99
Very Good 4.5 /5Review Score Call
Budget Inn of Aberdeen : 1112 South Philadelphia Blvd.
+1-800-230-4134
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Cheap Downtown hotel
  • Check-in: 12.00
Wingate by Wydham : 1326 Poilicy Dr. 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • 3-star Suburban property
  • 107 rooms in property
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Economical Suburban hotel
  • Check in time: 11:00 am
Motel 6 Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Two star Highway hotel
  • Fitness center on property
The Inn at the Chesapeake Bay Beach Club - Stevensville 180 Pier One Rd., Stevensville, MD 21666 ~21.19 miles southwest of Chestertown
  • Four star Resort property
  • Hotel has 12 suites
From$169
Very Good 4.5 /5Review Score Call
Ramada Conference Center
+1-800-997-5149
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • 2 star Suburban property
  • Check in time: 3:00pm
Candlewood Suites Bel Air - Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • 2 star Suburban property
  • Fitness center on property
From$65
Very Good 4.0 /5Read Reviews Call
Holiday Inn Express in Edgewood
+1-800-230-4134
2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Mid-scale Suburban hotel
  • Fitness center on property
From$119
Very Good 4.0 /5Review Score Call
Extended Stay America Bel Air : 1361 James Way 1361 James Way, Bel Air, MD 21015 ~21.26 miles northwest of Chestertown
  • Two star Highway hotel
  • 101 rooms in property
Comfort Inn & Suites Edgewood Aberdeen Bel Air - Edgewood 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Low priced Suburban hotel
  • Free breakfast available
Homewood Suites by Hilton in Bel Air
+1-888-305-3366
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • 3 star Suburban hotel
  • 92 suites in hotel
From$124
Very Good 4.5 /5Reviews Call
Springhill Suites by Marriott Edgewood Aberdeen : 1420 Handlir Dr. 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Affordable Highway hotel
  • Check in: 3:00pm
From$99
Very Good 4.0 /5Review Score Call
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Mid-scale Rural hotel
  • Hotel has 3 floors
Hampton Inn & Suites Edgewood / Aberdeen South : 2110 Emmorton Park Rd. 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • 3-star Suburban hotel
  • Fitness center on property
From$89
Very Good 4.5 /5Read Reviews Call
La Quinta Inn & Suites Edgewood Aberdeen Bel Air 2112b Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Three Star Suburban property
  • Hotel has 66 rooms
Historic Kent Manor Inn & Events
+1-800-997-5148
500 Kent Manor Dr., Stevensville Kent Island Annapolis, MD 21666 ~21.59 miles southwest of Chestertown
  • Four-star Riverfront hotel
  • 24 rooms in property
From$135
Very Good 4.5 /5Reviews Call
Super 8
+1-888-690-5247
98 Stemmers Run Rd., Essex, MD 21221 ~22.10 miles west of Chestertown
  • 2 star Rural property
  • Shuttle from airport available
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