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., Chestertown, MD 21620
  • Two star Riverfront hotel
  • Hotel has 27 rooms
Comfort Suites : 160 Scheeler Rd.
+1-800-230-4134
160 Scheeler Rd., Chestertown, MD 21620
  • Mid-scale Rural property
  • Hotel has 53 rooms
From$75
Very Good 4.0 /5 Guest Reviews Call
Holiday Inn Express & Suites Chestertown Md in Chestertown 150 Scheeler Rd., Chestertown, MD 21620
  • Three Star Suburban property
  • Check-in time: 3:00pm
From$115
Very Good 4.0 /5 Hotel Reviews Call
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • 4 star Rural hotel
  • 3 floors in hotel
Holiday Inn Express Kent Island / Annapolis East
+1-888-305-3366
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Three Star Rural property
  • 76 rooms in hotel
From$80
Very Good 4.0 /5 Read Reviews Call
Best Western Kent Narrows Inn in Grasonville 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Economical Resort hotel
  • Complimentary breakfast is offered
From$80
Average 3.5 /5 Reviews Call
Hilton Garden Inn Kent Island 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • 3-star Riverfront hotel
  • Check-in time: 03:00PM
From$137
Very Good 4.5 /5 Recent 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
  • Economical Resort property
  • Free complimentary breakfast
From$75
Very Good 4.0 /5 Hotel Reviews Call
Home2 Suites by Hilton Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • 3 star Suburban property
  • Gym / Fitness Center Available
From$99
Very Good 4.5 /5 Read Reviews Call
Budget Inn of Aberdeen - Aberdeen
+1-800-997-5148
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Low-priced Downtown hotel
  • 4 suites in hotel
From$64
Very Good 4.5 /5 Reviews Call
Wingate by Wyndham 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • Affordable Suburban property
  • 107 sleeping rooms in hotel
From$60
Average 3.5 /5 Hotel Reviews Call
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • 2-star Suburban hotel
  • Free breakfast available
From$65
Very Good 4.0 /5 Guest Reviews Call
Motel 6 Edgewood : 1709 Edgewood Rd. 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Economical Highway hotel
  • Hotel has 22 suites
From$43
Poor 2.5 /5 Reviews Call
The Inn at the Chesapeake Bay Beach Club 180 Pier One Rd., Stevensville, MD 21666 ~21.19 miles southwest of Chestertown
  • Four-star Resort hotel
  • 12 suites in hotel
From$169
Very Good 4.5 /5 Guest Reviews Call
Ramada Conference Center : 1700 Van Bibber Rd.
+1-888-690-5281
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Two-star Suburban property
  • 3 suites in hotel
From$59
Average 3.0 /5 Review Score Call
Candlewood Suites Bel Air - Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Low-priced Suburban hotel
  • 95 rooms in property
From$65
Very Good 4.0 /5 Reviews Call
Holiday Inn Express 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • 3-star Suburban property
  • 6 suites in hotel
From$119
Very Good 4.0 /5 Reviews Call
Extended Stay America Bel Air : 1361 James Way 1361 James Way, Bel Air, MD 21015 ~21.26 miles northwest of Chestertown
  • Economical Highway property
  • Check-in: 3:00pm
From$47
Average 3.0 /5 Read Reviews Call
Comfort Inn & Suites Edgewood Aberdeen Bel Air 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Low-priced Suburban property
  • Hotel has 20 suites
From$57
Very Good 4.0 /5 Recent Reviews Call
Homewood Suites by Hilton : 4170 Philadelphia Rd.
+1-800-881-1523
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Midscale Suburban hotel
  • Hotel has 5 floors
From$159
Very Good 4.5 /5 Read Reviews Call
Springhill Suites by Marriott Edgewood Aberdeen - Bel Air 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Affordable Highway property
  • Hotel has 119 suites
From$99
Very Good 4.0 /5 Read Reviews Call
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Midscale Rural hotel
  • Free complimentary breakfast
From$75
Very Good 4.5 /5 Read 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 property
  • Free breakfast available
From$89
Very Good 4.5 /5 Read Reviews Call
La Quinta Inn & Suites Edgewood Aberdeen Bel Air 2112b Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Affordable Suburban hotel
  • Complimentary breakfast is offered
From$62
Very Good 4.5 /5 Read Reviews Call
Historic Kent Manor Inn & Events : 500 Kent Manor Dr.
+1-888-690-5247
500 Kent Manor Dr., Stevensville Kent Island Annapolis, MD 21666 ~21.59 miles southwest of Chestertown
  • High-end Riverfront hotel
  • 4 conference rooms in property
From$135
Very Good 4.5 /5 Recent Reviews Call
Next 25 Chestertown Hotels >   [1 - 25 of 50]    
Next: See My Chestertown Hotels with Pricing
Back to Top