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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 609 Washington Ave., Chestertown, MD 21620
  • 2-star Riverfront property
  • 27 rooms in hotel
  • Rooms need regular maintenance
  • Hotel buildings could use some improvement
Quality Suites 160 Scheeler Rd., Chestertown, MD 21620
  • 3-star Rural hotel
  • 53 rooms in hotel
Holiday Inn Express & Suites Chestertown Md : 150 Scheeler Rd. 150 Scheeler Rd., Chestertown, MD 21620
  • 3 star Suburban hotel
  • Gym is available on property
From$162
Very Good 4.0 /5Guest Reviews Call
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • Expensive Rural hotel
  • 3 floors in property
Sleep Inn
+1-888-305-3366
101 Vfw Ave., Grasonville, MD 21638 ~18.60 miles southwest of Chestertown
  • Cheap Resort hotel
  • Free complimentary breakfast
Holiday Inn Express Kent Island / Annapolis East 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Three Star Rural hotel
  • Check-in: 3:00pm
  • Close to marina
  • Great view
From$80
Very Good 4.0 /5Review Score Call
Best Western Kent Narrows Inn - Grasonville 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • 2-star Resort property
  • Free breakfast
  • Management should be more attentive
  • Carpets sticky
Hilton Garden Inn Kent Island 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • 3-star Riverfront property
  • Hotel has 30 suites
  • Facilities available
  • Homey feeling
From$124
Very Good 4.5 /5Review Score Call
Home2 Suites by Hilton Aberdeen in Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • 3-star Suburban hotel
  • 107 suites in hotel
Budget Inn of Aberdeen
+1-800-230-4134
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Two-star Downtown property
  • 25 rooms in property
  • Room is all right
  • Rather comfortable
From$64
Very Good 4.5 /5Reviews Call
Arborview at Riverside in Liriope : 1307 Liriope Court 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • 4 star property
  • Check in: 4:00 p.m.
Wingate by Wyndham 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • Midscale Suburban property
  • 3 floors in hotel
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Economical Suburban property
  • 3 floors in property
  • Comfortable beds
  • Friendly service
Motel 6 Edgewood - Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • 2 star Highway property
  • 22 suites in property
Ramada Conference Center : 1700 Van Bibber Rd.
+1-888-283-3404
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Low-priced Suburban property
  • Check-in: 3:00pm
  • Cleanliness of the bathroom was average, said 50%
  • Close to restaurants and bars
Candlewood Suites Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Cheap Suburban hotel
  • Hotel has 95 suites
  • Friendly staff
  • Location is great
Extended Stay America Baltimore Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • 2 star Highway hotel
  • Free complimentary breakfast
From$104
Average 3.0 /5Reviews Call
Holiday Inn Express 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Midscale Suburban hotel
  • 6 suites in hotel
  • Terrific location
  • Most guests found the staff to be very friendly
From$119
Very Good 4.0 /5Latest Reviews Call
Comfort Inn & Suites Edgewood Aberdeen Bel Air : 2112a Emmorton Park Rd. 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Low Cost Suburban property
  • Hotel has 104 rooms
  • Good accessibility by car
  • Easily accessible by car and has restaurants and bars nearby
Homewood Suites by Hilton - Bel Air
+1-888-690-5247
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Hotel has 92 suites
  • Most guests found the staff to be very friendly
  • Conveniently located
From$159
Very Good 4.5 /5Review Score 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
  • Check in: 3:00pm
  • Separate living area
  • All guests said rooms were clean
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
  • Hotel has 3 floors
  • Rather comfortable
  • Good wifi quality
The Inn at the Chesapeake Bay Beach Club & Spa 180 Pier One Rd., Stevensville, MD 21666 ~21.35 miles southwest of Chestertown
  • High end Suburban property
  • Fitness / Gym is on-site
From$162
Very Good 4.5 /5Recent Reviews Call
Hampton Inn & Suites Edgewood / Aberdeen South 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Midscale Suburban hotel
  • Check in time: 12:00 PM
  • Spacious rooms
  • Most guests thought the building was wonderful
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
  • Midscale Suburban hotel
  • 66 sleeping rooms in hotel
  • Free WLAN
  • Most guests complained about the elevator
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