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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

Driftwood Inn in Chestertown 609 Washington Ave., Chestertown, MD 21620
  • Cheap Riverfront property
  • Hotel has 3 suites
Comfort Suites : 160 Scheeler Rd.
+1-800-230-4134
160 Scheeler Rd., Chestertown, MD 21620
  • Midscale Rural hotel
  • 53 sleeping rooms in hotel
From$75
Very Good 4.0 /5 Hotel Reviews Call
Holiday Inn Express & Suites Chestertown Md - Chestertown 150 Scheeler Rd., Chestertown, MD 21620
  • 3-star Suburban property
  • Check-in time: 3:00pm
From$115
Very Good 4.0 /5 Review Score Call
Brampton Inn in Chestertown 25227 Chestertown Rd., Chestertown, MD 21620
  • Four star Rural property
  • 6 suites in property
Holiday Inn Express Kent Island / Annapolis East : 1020 Kent Narrows Rd.
+1-888-305-3366
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Mid-scale Rural property
  • Hotel has 3 floors
From$80
Very Good 4.0 /5 Review Score Call
Best Western Kent Narrows Inn - Grasonville 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Low-priced Resort property
  • Gym is available on property
From$80
Average 3.5 /5 Guest Reviews Call
Hilton Garden Inn Kent Island in Grasonville 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Mid-scale Riverfront property
  • Hotel has 30 suites
From$137
Very Good 4.5 /5 Reviews Call
Sleep Inn Grasonville Md. in Grasonville
+1-888-690-5281
101 V.f.w Ave., Grasonville, MD 21638 ~19.69 miles south of Chestertown
  • Cheap Resort hotel
  • Complimentary breakfast is offered
From$75
Very Good 4.0 /5 Recent Reviews Call
Home2 Suites by Hilton Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • 3 star Suburban hotel
  • Fitness + Health Center
From$99
Very Good 4.0 /5 Latest Reviews Call
Budget Inn of Aberdeen
+1-800-997-5148
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Two star Downtown property
  • Check in time: 12.00
From$64
Very Good 4.5 /5 Read Reviews Call
Arborview at Riverside in Liriope 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • Expensive hotel
  • Hotel has 12 rooms
Wingate by Wyndham in Belcamp 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Complimentary breakfast is offered
From$62
Average 3.5 /5 Latest Reviews Call
Sleep Inn & Suites : 1807 Edgewood Rd. 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Low priced Suburban property
  • 3 floors in property
From$65
Very Good 4.0 /5 Hotel Reviews Call
Motel 6 Edgewood - Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • 2 star Highway hotel
  • 22 suites in hotel
The Inn at the Chesapeake Bay Beach Club 180 Pier One Rd., Stevensville, MD 21666 ~21.19 miles southwest of Chestertown
  • High end Resort property
  • 4 floors in hotel
From$162
Very Good 4.5 /5 Latest Reviews Call
Ramada Conference Center : 1700 Van Bibber Rd.
+1-800-230-4134
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Low-priced Suburban hotel
  • 152 rooms in property
From$59
Average 3.0 /5 Guest Reviews Call
Candlewood Suites Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Inexpensive Suburban hotel
  • 95 suites in property
From$65
Very Good 4.0 /5 Review Score Call
Holiday Inn Express 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • 3-star Suburban property
  • Complimentary breakfast is offered
From$119
Very Good 4.0 /5 Latest Reviews Call
Extended Stay America Bel Air in Bel Air 1361 James Way, Bel Air, MD 21015 ~21.26 miles northwest of Chestertown
  • Two-star Highway hotel
  • 101 rooms in hotel
From$47
Average 3.0 /5 Recent Reviews Call
Comfort Inn & Suites Edgewood Aberdeen Bel Air - Edgewood 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • 2 star Suburban property
  • Hotel has 104 rooms
From$57
Very Good 4.0 /5 Guest Reviews Call
Homewood Suites by Hilton in Bel Air
+1-800-997-5149
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Affordable Suburban hotel
  • 92 rooms in property
From$159
Very Good 4.5 /5 Review Score Call
Springhill Suites by Marriott Edgewood Aberdeen - Bel Air 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Three Star Highway property
  • Hotel has 119 suites
From$99
Very Good 4.0 /5 Hotel Reviews Call
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 - Bel Air 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Three Star Rural property
  • Hotel has a green policy See more
From$75
Very Good 4.5 /5 Latest Reviews Call
Hampton Inn & Suites Edgewood / Aberdeen South in Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Three Star Suburban hotel
  • Hotel has an eco-friendly policy See more
From$89
Very Good 4.5 /5 Guest 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
  • Three Star Suburban hotel
  • 3 floors in hotel
From$62
Very Good 4.5 /5 Read Reviews Call
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