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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. 609 Washington Ave., Chestertown, MD 21620
  • 2 star Riverfront property
  • Check in time: 2:00pm
  • No kitchen facilities
  • Service could be friendlier
Quality Suites in Chestertown 160 Scheeler Rd., Chestertown, MD 21620
  • Midscale Rural hotel
  • Free comp. breakfast
Holiday Inn Express & Suites Chestertown Md 150 Scheeler Rd., Chestertown, MD 21620
  • Three Star Suburban hotel
  • 81 sleeping rooms in hotel
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • 4 star Rural property
  • Check-in time: 3:00PM
Sleep Inn : 101 Vfw Ave.
+1-866-221-8581
101 Vfw Ave., Grasonville, MD 21638 ~18.60 miles southwest of Chestertown
  • Two star Resort property
  • 59 rooms in hotel
Holiday Inn Express Annapolis East / Kent Island 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • Three Star Rural hotel
  • Comp. Breakfast
From$180
Very Good 4.0 /5Read Reviews CallBookMore Details
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Economy Resort property
  • Free breakfast
  • Bathroom needs cleaning
  • Friendly service
From$67
Average 3.5 /5Reviews CallBookMore Details
Hilton Garden Inn Kent Island 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Three Star Riverfront property
  • Hotel has 4 meeting rooms
  • Nice building
  • Rooms need regular maintenance
From$124
Very Good 4.5 /5Recent Reviews CallBookMore Details
Home2 Suites by Hilton Aberdeen : 20 Newton Rd. 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Mid-scale Suburban property
  • 5 floors in property
Budget Inn of Aberdeen
+1-800-881-1523
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Economical Downtown property
  • Hotel has 4 suites
  • Rooms are ok
  • Bed spread was full of
From$64
Very Good 4.5 /5Read Reviews CallBookMore Details
Arborview at Riverside in Liriope 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • Four star hotel
  • Hotel has 3 floors
Wingate by Wyndham - Belcamp 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Hotel has 7 suites
From$69
Average 3.5 /5Reviews CallBookMore Details
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Economy Suburban property
  • Fitness center on property
  • Most guests complained about the bathroom
  • Tasty breakfast
From$65
Very Good 4.0 /5Review Score CallBookMore Details
Motel 6 Edgewood : 1709 Edgewood Rd. 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Low Cost Highway hotel
  • Hotel has 2 meeting rooms
Ramada Conference Center - Edgewood 1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Inexpensive Suburban property
  • 152 rooms in property
  • Great pool
  • Most guests said rooms were small
Candlewood Suites Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Inexpensive Suburban hotel
  • Fitness center on property
  • Great water pressure
  • Great reception
From$65
Very Good 4.0 /5Read Reviews CallBookMore Details
Extended Stay America Baltimore Bel Air - Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Two star Highway hotel
  • 101 suites in hotel
Holiday Inn Express 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Three Star Suburban hotel
  • Check in time: 3:00 pm
  • Most guests said the reception staff was great
  • World class service
From$119
Very Good 4.0 /5Hotel Reviews CallBookMore Details
Red Roof Inn Edgewood - Edgewood 2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • Low-priced property
Comfort Inn & Suites Edgewood Aberdeen Bel Air 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Economical Suburban property
  • Fitness / Gym is on-site
  • Good breakfast
  • World class service
From$57
Very Good 4.0 /5Reviews CallBookMore Details
Homewood Suites by Hilton : 4170 Philadelphia Rd.
+1-888-690-5281
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • 3 star Suburban property
  • 5 floors in hotel
  • Friendly service
  • Most guests thought rooms were spacious
From$159
Very Good 4.5 /5Latest Reviews CallBookMore Details
Springhill Suites by Marriott Edgewood Aberdeen : 1420 Handlir Dr. 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Affordable Highway hotel
  • Access to gym on-site
  • Bed was comfortable
  • Great rooms and fantastic service
From$96
Very Good 4.0 /5Read Reviews CallBookMore Details
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 in Bel Air 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Three Star Rural hotel
  • Gym is available on property
  • Yummy desserts, said 100%
  • The majority of guests liked the big bathroom
From$75
Very Good 4.5 /5Reviews CallBookMore Details
The Inn at the Chesapeake Bay Beach Club & Spa 180 Pier One Rd., Stevensville, MD 21666 ~21.35 miles southwest of Chestertown
  • 4-star Suburban property
  • Check in: 4:00 PM
From$162
Very Good 4.5 /5Review Score CallBookMore Details
Hampton Inn & Suites Edgewood / Aberdeen South in Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • 3 star Suburban property
  • Fitness + Health Center
  • Clean
  • Friendly service
From$89
Very Good 4.5 /5Reviews CallBookMore Details
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