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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

Driftwood Inn 609 Washington Ave., Chestertown, MD 21620
  • Cheap Riverfront hotel
  • 3 suites in property
Comfort Suites - Chestertown
+1-800-230-4134
160 Scheeler Rd., Chestertown, MD 21620
  • Mid-scale Rural property
  • Hotel has 53 rooms
From$75
Very Good 4.0 /5Reviews Call
Holiday Inn Express & Suites Chestertown Md - Chestertown 150 Scheeler Rd., Chestertown, MD 21620
  • 3 star Suburban hotel
  • 81 sleeping rooms in hotel
From$115
Very Good 4.0 /5Read Reviews Call
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • Four star Rural property
  • Check in time: 3:00PM
Holiday Inn Express Kent Island / Annapolis East in Grasonville
+1-888-305-3366
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • 3-star Rural property
  • 3 meeting rooms in hotel
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Two-star Resort hotel
  • Check-in: 3:00 PM
Hilton Garden Inn Kent Island - Grasonville 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Affordable Riverfront property
  • Check in: 03:00PM
From$137
Very Good 4.5 /5Recent Reviews Call
Sleep Inn Grasonville Md. - Grasonville
+1-888-690-5281
101 V.f.w Ave., Grasonville, MD 21638 ~19.69 miles south of Chestertown
  • 2-star Resort property
  • Hotel has 2 suites
Home2 Suites by Hilton Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Midscale Suburban hotel
  • Free complimentary breakfast
Budget Inn of Aberdeen : 1112 South Philadelphia Blvd.
+1-800-997-5148
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Low priced Downtown hotel
  • 4 suites in hotel
From$64
Very Good 4.5 /5Review Score Call
Wingate by Wyndham in Belcamp 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • 3 star Suburban property
  • 3 floors in property
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Low-priced Suburban property
  • 3 floors in property
Motel 6 Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • 2 star Highway hotel
  • 2 floors 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 property
From$162
Very Good 4.5 /5Hotel Reviews Call
Ramada Conference Center
+1-888-690-5281
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Two star Suburban hotel
  • Check in: 3:00pm
Candlewood Suites Bel Air : 4216 Philadelphia Rd. 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Two star Suburban hotel
  • Hotel has 95 suites
From$65
Very Good 4.0 /5Reviews Call
Holiday Inn Express 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • 3 star Suburban property
  • 92 sleeping rooms in hotel
From$119
Very Good 4.0 /5Guest Reviews Call
Extended Stay America Bel Air in Bel Air 1361 James Way, Bel Air, MD 21015 ~21.26 miles northwest of Chestertown
  • 2 star Highway hotel
  • Check in: 3:00pm
Comfort Inn & Suites Edgewood Aberdeen Bel Air 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Economy Suburban hotel
  • 104 rooms in property
Homewood Suites by Hilton
+1-800-881-1523
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • 3-star Suburban hotel
  • Gym is available on property
From$159
Very Good 4.5 /5Read 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
  • 119 rooms in property
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 : 1435 Handlir Dr. 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 /5Review Score Call
Hampton Inn & Suites Edgewood / Aberdeen South - Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • 3 star Suburban property
  • 34 suites in property
La Quinta Inn & Suites Edgewood Aberdeen Bel Air 2112b Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Three Star Suburban hotel
  • Check in: 3:00 PM
Historic Kent Manor Inn & Events in Stevensville Kent Island Annapolis
+1-888-690-5247
500 Kent Manor Dr., Stevensville Kent Island Annapolis, MD 21666 ~21.59 miles southwest of Chestertown
  • 4 star Riverfront property
  • Check in time: 3:00 pm
From$135
Very Good 4.5 /5Guest Reviews Call
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