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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
  • Inexpensive Riverfront hotel
  • Check in: 2:00pm
Comfort Suites
+1-800-230-4134
160 Scheeler Rd., Chestertown, MD 21620
  • Affordable Rural property
  • Hotel has 3 floors
Holiday Inn Express & Suites Chestertown Md : 150 Scheeler Rd. 150 Scheeler Rd., Chestertown, MD 21620
  • Three Star Suburban hotel
  • Fitness center on property
From$115
Very Good 4.0 /5Reviews Call
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • Four star Rural property
  • Check in: 3:00PM
Holiday Inn Express Kent Island / Annapolis East - Grasonville
+1-888-305-3366
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • 3 star Rural property
  • 3 floors in hotel
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Economical Resort property
  • Check-in: 3:00 PM
From$80
Average 3.5 /5Reviews Call
Hilton Garden Inn Kent Island : 3206 Main St. 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Midscale Riverfront hotel
  • 5 floors in property
From$137
Very Good 4.5 /5Latest Reviews Call
Sleep Inn Grasonville Md. : 101 V.f.w Ave.
+1-888-690-5281
101 V.f.w Ave., Grasonville, MD 21638 ~19.69 miles south of Chestertown
  • Inexpensive Resort hotel
  • Comp. Breakfast
Home2 Suites by Hilton Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • 3-star Suburban hotel
  • Complimentary breakfast is offered
Budget Inn of Aberdeen in Aberdeen
+1-800-997-5148
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Low-priced Downtown hotel
  • 25 sleeping rooms in hotel
Arborview at Riverside in Liriope - Belcamp 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • Four-star property
  • 12 sleeping rooms in hotel
Wingate by Wyndham 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • Midscale Suburban property
  • 3 floors in property
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Cheap Suburban property
  • Hotel has 84 rooms
From$65
Very Good 4.0 /5Review Score Call
Motel 6 Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Low Cost Highway property
  • Check-in: 3:00PM
The Inn at the Chesapeake Bay Beach Club 180 Pier One Rd., Stevensville, MD 21666 ~21.19 miles southwest of Chestertown
  • High end Resort hotel
  • 4 floors in hotel
From$162
Very Good 4.5 /5Latest 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
  • Cheap Suburban property
  • Free complimentary breakfast
Candlewood Suites Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • 2-star Suburban property
  • Check-in time: 3:00
Holiday Inn Express - Edgewood 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • 3 star Suburban property
  • Free comp. breakfast
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
  • Cheap Highway property
  • Hotel has 101 suites
Comfort Inn & Suites Edgewood Aberdeen Bel Air - Edgewood 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Two-star Suburban hotel
  • Check in: 3:00 PM
Homewood Suites by Hilton
+1-800-997-5149
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • 3 star Suburban property
  • Hotel has 5 floors
From$159
Very Good 4.5 /5Hotel Reviews Call
Springhill Suites by Marriott Edgewood Aberdeen : 1420 Handlir Dr. 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Midscale Highway hotel
  • Check-in time: 3:00pm
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • 3 star Rural hotel
  • Check in: 3pm
Hampton Inn & Suites Edgewood / Aberdeen South 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • 3 star Suburban hotel
  • 134 sleeping rooms in hotel
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
  • 3 star Suburban property
  • 66 suites in property
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