Star Rating
Hotel Name
Price Range (USD)to
Amenities

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. 609 Washington Ave., Chestertown, MD 21620
  • Inexpensive Riverfront hotel
  • Hotel has 27 rooms
Comfort Suites
+1-800-230-4134
160 Scheeler Rd., Chestertown, MD 21620
  • Midscale Rural hotel
  • 53 suites in hotel
Holiday Inn Express & Suites Chestertown Md - Chestertown 150 Scheeler Rd., Chestertown, MD 21620
  • Three Star Suburban hotel
  • Free breakfast available
From$115
Very Good 4.0 /5Hotel Reviews Call
Brampton Inn - Chestertown 25227 Chestertown Rd., Chestertown, MD 21620
  • High-end Rural hotel
  • Check-in: 3:00PM
Holiday Inn Express Kent Island / Annapolis East in Grasonville
+1-888-305-3366
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Affordable Rural hotel
  • Check in: 3:00pm
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Two-star Resort hotel
  • Check-in time: 3:00 PM
Hilton Garden Inn Kent Island in Grasonville 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Affordable Riverfront property
  • 90 sleeping rooms in hotel
From$132
Very Good 4.5 /5Read Reviews Call
Sleep Inn Grasonville Md. in Grasonville
+1-888-690-5281
101 V.f.w Ave., Grasonville, MD 21638 ~19.69 miles south of Chestertown
  • 2 star Resort property
  • Free complimentary breakfast
Home2 Suites by Hilton Aberdeen - Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Three Star Suburban hotel
  • 107 suites in hotel
From$99
Very Good 4.5 /5Review Score Call
Budget Inn of Aberdeen - Aberdeen
+1-800-997-5148
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • 2 star Downtown property
  • Check-in time: 12.00
Wingate by Wyndham 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • 3 star Suburban property
  • Hotel has 3 meeting rooms
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Economical Suburban hotel
  • Fitness center on property
Motel 6 Edgewood in Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Economical Highway hotel
  • Gym is available on property
The Inn at the Chesapeake Bay Beach Club : 180 Pier One Rd. 180 Pier One Rd., Stevensville, MD 21666 ~21.19 miles southwest of Chestertown
  • 4-star Resort property
  • 54 rooms in property
From$169
Excellent 5.0 /5Review Score Call
Ramada Conference Center in Edgewood
+1-888-690-5281
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Low Cost Suburban hotel
  • 2 floors in hotel
Candlewood Suites Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Economy Suburban hotel
  • 3 floors in property
From$65
Very Good 4.0 /5Reviews 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
  • Fitness / Gym is on-site
From$119
Very Good 4.0 /5Guest Reviews Call
Extended Stay America Bel Air - Bel Air 1361 James Way, Bel Air, MD 21015 ~21.26 miles northwest of Chestertown
  • Low-priced Highway property
  • Check-in time: 3:00pm
From$47
Average 3.0 /5Reviews Call
Comfort Inn & Suites Edgewood Aberdeen Bel Air 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Cheap Suburban hotel
  • Fitness center on property
Homewood Suites by Hilton : 4170 Philadelphia Rd.
+1-800-881-1523
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • 3-star Suburban property
  • Hotel has 92 suites
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
  • Mid-scale Highway property
  • 3 floors in property
From$99
Very Good 4.0 /5Read Reviews Call
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
  • Mid-scale Rural property
  • Fitness center on property
From$75
Very Good 4.5 /5Reviews Call
Hampton Inn & Suites Edgewood / Aberdeen South : 2110 Emmorton Park Rd. 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Three Star Suburban hotel
  • Free breakfast available
From$89
Very Good 4.5 /5Reviews Call
La Quinta Inn & Suites Edgewood Aberdeen Bel Air - Edgewood 2112b Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Mid-scale Suburban hotel
  • Free breakfast available
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
  • 24 sleeping rooms in hotel
From$135
Very Good 4.5 /5Guest Reviews Call
Next 25 Chestertown Hotels >  [1 - 25 of 50]    
Next: See My Chestertown Hotels with Pricing
Back to Top