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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
  • Low Cost Riverfront property
  • Check-in time: 2:00pm
  • Hotel facilities could use a good clean
  • Awful rooms
Comfort Suites in Chestertown
+1-800-230-4134
160 Scheeler Rd., Chestertown, MD 21620
  • Midscale Rural property
  • Check-in: 3:00pm
  • Noise level is acceptable
  • Cushions were worn
Holiday Inn Express & Suites Chestertown Md : 150 Scheeler Rd. 150 Scheeler Rd., Chestertown, MD 21620
  • 3 star Suburban property
  • Gym / Fitness Center Available
From$162
Very Good 4.0 /5Latest Reviews Call
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • Four star Rural property
  • 3 floors in hotel
Holiday Inn Express Kent Island / Annapolis East in Grasonville 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Affordable Rural property
  • Free breakfast
  • Close to marina
  • Hotel looks new
From$80
Very Good 4.0 /5Review Score Call
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Low Cost Resort hotel
  • Free complimentary breakfast
  • Hotel buildings could use some improvement
  • High price
Hilton Garden Inn Kent Island 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Affordable Riverfront hotel
  • Gym / Fitness Center Available
  • Lowest price
  • Best rates
From$124
Very Good 4.5 /5Latest Reviews Call
Sleep Inn Grasonville Md. in Grasonville
+1-800-997-5149
101 V.f.w Ave., Grasonville, MD 21638 ~19.69 miles south of Chestertown
  • Inexpensive Resort property
  • 59 rooms in hotel
  • Good service
  • Bathrooms Are Small
Home2 Suites by Hilton Aberdeen - Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • 3 star Suburban property
  • 5 floors in property
From$99
Very Good 4.0 /5Reviews Call
Budget Inn of Aberdeen
+1-800-230-4134
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Economy Downtown property
  • 25 rooms in property
  • Most guests said rooms were clean enough
  • Popular among solo travelers
From$64
Very Good 4.5 /5Review Score Call
Arborview at Riverside in Liriope - Belcamp 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • Four-star property
  • Check-in time: 4:00 p.m.
Wingate by Wyndham : 1326 Poilicy Dr. 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • Affordable Suburban property
  • 107 rooms in hotel
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Cheap Suburban hotel
  • Free complimentary breakfast
  • Most guests found the staff to be very friendly
  • Most guests thought the atmosphere was somewhat friendly
Motel 6 Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Cheap Highway hotel
  • Check in: 3:00PM
Ramada Conference Center - Edgewood
+1-888-283-3404
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • 2-star Suburban hotel
  • Gym is available on property
  • Cleaning crew clean
  • Room was not clean
Candlewood Suites Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Low Cost Suburban property
  • 3 floors in property
  • Most guests found the staff to be very friendly
  • Great room
Extended Stay America Baltimore Bel Air in Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Cheap Highway property
  • 3 floors in hotel
Holiday Inn Express 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Mid-scale Suburban property
  • 6 suites in property
  • Most guests said rooms were clean
  • Breakfast is good
From$119
Very Good 4.0 /5Read Reviews Call
Comfort Inn & Suites Edgewood Aberdeen Bel Air in Edgewood 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Low priced Suburban property
  • Fitness + Health Center
  • Most guests thought it was clean
  • Dated rooms
From$60
Very Good 4.5 /5Reviews Call
Homewood Suites by Hilton
+1-888-690-5247
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Affordable Suburban hotel
  • Free complimentary breakfast
  • Clean Rooms
  • Conveniently located
From$159
Very Good 4.5 /5Guest Reviews Call
Springhill Suites by Marriott Edgewood Aberdeen 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Mid-scale Highway property
  • Check in time: 3:00pm
  • Average sized rooms
  • Every guests reviewed said the beds were comfortable
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
  • Affordable Rural hotel
  • Fitness + Health Center
  • Comfortable beds
  • Noise level is acceptable
From$75
Very Good 4.5 /5Read Reviews Call
The Inn at the Chesapeake Bay Beach Club - Stevensville 180 Pier One Rd., Stevensville, MD 21666 ~21.35 miles southwest of Chestertown
  • High end Suburban property
  • Hotel has a green policy See more
From$162
Very Good 4.5 /5Recent Reviews Call
Hampton Inn & Suites Edgewood / Aberdeen South in Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Midscale Suburban hotel
  • 134 sleeping rooms in hotel
  • Most guests said rooms were clean
  • Good location
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
  • Free breakfast available
  • Very good family hotel
  • Most guests thought rooms were spacious
From$65
Very Good 4.5 /5Review Score Call
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