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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, Motels & Accommodations

Comfort Suites : 160 Scheeler Rd.
+1-888-690-5281
160 Scheeler Rd., Chestertown, MD 21620
  • Three Star Rural property
  • Hotel has 53 rooms
From$75
Very Good 4.0 /5 Guest Reviews Call
Holiday Inn Express & Suites Chestertown Md : 150 Scheeler Rd. 150 Scheeler Rd., Chestertown, MD 21620
  • Three Star Suburban hotel
  • Free complimentary breakfast
From$115
Very Good 4.0 /5 Recent Reviews Call
Brampton Inn - Chestertown 25227 Chestertown Rd., Chestertown, MD 21620
  • High-end Rural hotel
  • Hotel has an eco-friendly policy See policy
Holiday Inn Express Kent Island / Annapolis East
+1-888-690-5247
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Affordable Rural hotel
  • Check-in time: 3:00pm
From$80
Very Good 4.0 /5 Latest Reviews Call
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Economical Resort property
  • Hotel has 4 floors
From$74
Average 3.5 /5 Hotel Reviews Call
Hilton Garden Inn Kent Island in Grasonville 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • 3 star Riverfront hotel
  • 90 rooms in property
From$132
Very Good 4.5 /5 Read Reviews Call
Sleep Inn Grasonville Md. : 101 V.f.w Ave.
+1-800-997-5149
101 V.f.w Ave., Grasonville, MD 21638 ~19.69 miles south of Chestertown
  • Two-star Resort property
  • Check-in: 3:00 PM
From$75
Very Good 4.0 /5 Hotel Reviews Call
Home2 Suites by Hilton Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • 3 star Suburban hotel
  • Check-in: 3:00PM
From$99
Very Good 4.5 /5 Hotel Reviews Call
Budget Inn of Aberdeen in Aberdeen
+1-800-230-4134
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Low-priced Downtown hotel
  • 25 rooms in property
From$64
Very Good 4.5 /5 Latest Reviews Call
Wingate by Wyhdham - Belcamp 1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • 3-star Suburban hotel
  • 107 sleeping rooms in hotel
From$60
Average 3.5 /5 Read Reviews Call
Sleep Inn & Suites - Edgewood 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Inexpensive Suburban hotel
  • 84 rooms in hotel
From$65
Average 3.5 /5 Reviews Call
Motel 6 Edgewood : 1709 Edgewood Rd. 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Low priced Highway hotel
  • 134 rooms in property
Ramada Conference Center - Edgewood
+1-800-881-1523
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Cheap Suburban hotel
  • Complimentary breakfast is offered
From$59
Average 3.0 /5 Review Score Call
Candlewood Suites Bel Air - Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Cheap Suburban hotel
  • Fitness / Gym is on-site
From$65
Very Good 4.0 /5 Hotel Reviews Call
Holiday Inn Express in Edgewood
+1-888-690-5281
2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • 3-star Suburban hotel
  • 3 floors in hotel
From$119
Very Good 4.0 /5 Read Reviews Call
Extended Stay America Bel Air - Bel Air 1361 James Way, Bel Air, MD 21015 ~21.26 miles northwest of Chestertown
  • Cheap Highway hotel
  • Check in: 3:00pm
From$47
Average 3.5 /5 Guest Reviews Call
Comfort Inn & Suites Edgewood Aberdeen Bel Air 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Low priced Suburban hotel
  • 20 suites in property
From$57
Very Good 4.0 /5 Read Reviews Call
Homewood Suites by Hilton : 4170 Philadelphia Rd.
+1-888-690-5247
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Midscale Suburban hotel
  • Fitness + Health Center
From$124
Very Good 4.5 /5 Recent Reviews Call
Springhill Suites by Marriott Edgewood Aberdeen : 1420 Handlir Dr. 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • 3 star Highway property
  • Hotel has 119 suites
From$99
Very Good 4.0 /5 Read Reviews Call
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 in Bel Air 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Midscale Rural property
  • Check-in: 3pm
From$75
Very Good 4.5 /5 Read Reviews Call
Hampton Inn & Suites Edgewood / Aberdeen South in Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Affordable Suburban hotel
  • Has environment-friendly policy Read more
From$89
Very Good 4.5 /5 Latest Reviews Call
La Quinta Inn & Suites Edgewood Aberdeen Bel Air : 2112b Emmorton Park Rd. 2112b Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • 3 star Suburban property
  • Check in: 3:00 PM
From$62
Very Good 4.5 /5 Hotel Reviews Call
Historic Kent Manor Inn & Events : 500 Kent Manor Dr.
+1-800-230-4134
500 Kent Manor Dr., Stevensville Kent Island Annapolis, MD 21666 ~21.59 miles southwest of Chestertown
  • Four star Riverfront property
  • 4 conference rooms in property
From$135
Very Good 4.5 /5 Latest Reviews Call
Super 8
+1-800-997-5148
98 Stemmers Run Rd., Essex, MD 21221 ~22.10 miles west of Chestertown
  • Low priced Rural hotel
  • Airport shuttle available
Super 8 Aberdeen
+1-888-690-5247
1008 Beards Hill Rd., Aberdeen, MD 21001 ~22.49 miles north of Chestertown
  • Low Cost hotel
  • 62 sleeping rooms in hotel
From$49
Average 3.0 /5 Recent Reviews Call
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