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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
  • Check-in: 2:00pm
Comfort Suites in Chestertown
+1-800-230-4134
160 Scheeler Rd., Chestertown, MD 21620
  • Three Star Rural property
  • Check in: 3:00pm
From$75
Very Good 4.0 /5 Latest Reviews Call
Holiday Inn Express & Suites Chestertown Md - Chestertown 150 Scheeler Rd., Chestertown, MD 21620
  • 3 star Suburban property
  • 20 suites in property
From$115
Very Good 4.0 /5 Recent Reviews Call
Brampton Inn - Chestertown 25227 Chestertown Rd., Chestertown, MD 21620
  • High end Rural property
  • Check-in time: 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
  • Mid-scale Rural hotel
  • Free breakfast
From$80
Very Good 4.0 /5 Guest Reviews Call
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • 2-star Resort property
  • 4 floors in hotel
From$80
Average 3.5 /5 Recent Reviews Call
Hilton Garden Inn Kent Island 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • 3-star Riverfront property
  • 5 floors in property
From$137
Very Good 4.5 /5 Hotel Reviews Call
Sleep Inn Grasonville Md.
+1-888-690-5281
101 V.f.w Ave., Grasonville, MD 21638 ~19.69 miles south of Chestertown
  • 2-star Resort property
  • 2 floors in property
From$75
Very Good 4.0 /5 Guest Reviews Call
Home2 Suites by Hilton Aberdeen : 20 Newton Rd. 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Three Star Suburban hotel
  • Free breakfast
From$99
Very Good 4.5 /5 Review Score Call
Budget Inn of Aberdeen
+1-800-997-5148
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Inexpensive Downtown hotel
  • Hotel has 25 rooms
From$64
Very Good 4.5 /5 Recent Reviews Call
Wingate by Wyndham 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • Mid-scale Suburban property
  • 107 rooms in hotel
From$60
Average 3.5 /5 Recent Reviews Call
Sleep Inn & Suites in Edgewood 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • 2-star Suburban hotel
  • 16 suites in hotel
From$65
Very Good 4.0 /5 Review Score Call
Motel 6 Edgewood : 1709 Edgewood Rd. 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • 2-star Highway property
  • Hotel has 22 suites
The Inn at the Chesapeake Bay Beach Club - Stevensville 180 Pier One Rd., Stevensville, MD 21666 ~21.19 miles southwest of Chestertown
  • High-end Resort hotel
  • Gym / Fitness Center Available
From$169
Very Good 4.5 /5 Reviews Call
Ramada Conference Center in Edgewood
+1-888-690-5281
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Cheap Suburban hotel
  • 4 meeting rooms in property
From$59
Average 3.0 /5 Reviews Call
Candlewood Suites Bel Air - Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Cheap Suburban hotel
  • 3 floors in property
From$65
Very Good 4.0 /5 Hotel Reviews Call
Holiday Inn Express : 2118 Emmorton Park Rd. 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • 3-star Suburban hotel
  • Check-in: 3:00 pm
From$119
Very Good 4.0 /5 Hotel Reviews Call
Extended Stay America Bel Air 1361 James Way, Bel Air, MD 21015 ~21.26 miles northwest of Chestertown
  • Economy Highway hotel
  • 101 suites in property
From$47
Average 3.0 /5 Latest Reviews Call
Comfort Inn & Suites Edgewood Aberdeen Bel Air 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Economy Suburban hotel
  • Fitness / Gym is on-site
From$57
Very Good 4.0 /5 Hotel Reviews Call
Homewood Suites by Hilton
+1-800-881-1523
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Affordable Suburban property
  • 92 rooms in property
From$159
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
  • Midscale Highway property
  • Free breakfast
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
  • Mid-scale Rural property
  • Gym is available on property
From$75
Very Good 4.5 /5 Reviews Call
Hampton Inn & Suites Edgewood / Aberdeen South - Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Mid-scale Suburban property
  • Hotel has an eco-friendly policy See more
From$89
Very Good 4.5 /5 Recent Reviews Call
La Quinta Inn & Suites Edgewood Aberdeen Bel Air 2112b Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Mid-scale Suburban hotel
  • 66 suites in hotel
From$62
Very Good 4.5 /5 Review Score Call
Historic Kent Manor Inn & Events
+1-888-690-5247
500 Kent Manor Dr., Stevensville Kent Island Annapolis, MD 21666 ~21.59 miles southwest of Chestertown
  • 4 star Riverfront hotel
  • Hotel has 4 meeting rooms
From$135
Very Good 4.5 /5 Reviews Call
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