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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. 609 Washington Ave., Chestertown, MD 21620
  • Economy Riverfront hotel
  • 27 rooms in hotel
  • Rooms in need of an update
  • Horrible vibe
Quality Suites 160 Scheeler Rd., Chestertown, MD 21620
  • 3 star Rural hotel
  • Check in time: 3.00 p.m
Holiday Inn Express & Suites Chestertown Md : 150 Scheeler Rd. 150 Scheeler Rd., Chestertown, MD 21620
  • 3-star Suburban hotel
  • Fitness center on property
From$95
Very Good 4.0 /5Reviews CallBookMore Details
Brampton Inn : 25227 Chestertown Rd. 25227 Chestertown Rd., Chestertown, MD 21620
  • 4-star Rural hotel
  • 13 rooms in hotel
Sleep Inn Grasonville 101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • Two star Resort hotel
  • Free breakfast available
Holiday Inn Express Annapolis East / Kent Island - Grasonville 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • Affordable Rural property
  • Check-in time: 3:00pm
From$180
Very Good 4.0 /5Review Score CallBookMore Details
Best Western Kent Narrows Inn - Grasonville 3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • Low Cost Resort property
  • Check in time: 4:00 PM
  • Room is all right
  • Friendly staff
From$67
Average 3.5 /5Reviews CallBookMore Details
Hilton Garden Inn Kent Island : 3206 Main St. 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Affordable Riverfront property
  • Hotel has 5 floors
  • Nice lobby
  • Excellent location
From$139
Very Good 4.5 /5Recent Reviews CallBookMore Details
Home2 Suites by Hilton Aberdeen in Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • 3-star Suburban hotel
  • Fitness / Gym is on-site
From$104
Very Good 4.0 /5Latest Reviews CallBookMore Details
Budget Inn of Aberdeen - Aberdeen
+1-800-881-1523
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Inexpensive Downtown hotel
  • Good budget hotel
  • Room is all right
Arborview at Riverside in Liriope - Belcamp 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • High-end hotel
  • Check in: 4:00 p.m.
Wingate by Wyndham 1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Mid-scale Suburban hotel
  • Access to gym on-site
From$69
Average 3.5 /5Reviews CallBookMore Details
Holiday Inn : 1326 Policy Dr. 1326 Policy Dr., Belcamp, MD 21017 ~21.04 miles northwest of Chestertown
  • Affordable Suburban hotel
  • Check-in: 3pm
Sleep Inn & Suites - Edgewood 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Low Cost Suburban property
  • Free comp. breakfast
  • Staff was great
  • Pool water was cold
Motel 6 Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Economical Highway hotel
  • Check-in: 3:00PM
Ramada Conference Center 1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Cheap Suburban property
  • 2 floors in property
  • Free breakfast
  • AC worked great
Candlewood Suites Bel Air : 4216 Philadelphia Rd. 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Economical Suburban property
  • 95 rooms in hotel
  • Room was nice and clean
  • Most guests thought the cleanliness of the hotel was average
From$65
Very Good 4.0 /5Review Score CallBookMore Details
Extended Stay America Baltimore Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • 2-star Highway property
  • Check-in: 3:00pm
Holiday Inn Express 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • 3 star Suburban property
  • Check-in: 3:00 pm
  • Friendly service
  • For breakfast was good
From$119
Very Good 4.0 /5Hotel Reviews CallBookMore Details
Red Roof Inn Edgewood 2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • Low priced property
Comfort Inn & Suites Edgewood Aberdeen 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Two star Suburban hotel
  • 104 sleeping rooms in hotel
  • Vibe is not too good
  • Free Breakfast offered
From$60
Very Good 4.0 /5Review Score CallBookMore Details
Homewood Suites by Hilton - Bel Air
+1-888-690-5247
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Affordable Suburban hotel
  • Hotel has 92 rooms
  • Most guests said the reception staff was great
  • Excellent breakfast
From$159
Very Good 4.5 /5Reviews CallBookMore Details
Springhill Suites by Marriott Edgewood Aberdeen in Bel Air 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Midscale Highway property
  • Free breakfast available
  • Reasonable pricing
  • Most guests said rooms were big enough
From$109
Very Good 4.0 /5Reviews 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
  • 3 star Rural hotel
  • Check-in time: 3pm
  • Almost all guests thought rooms were spacious
  • For only 67%, the noise level was all right
The Inn at the Chesapeake Bay Beach Club & Spa in Stevensville 180 Pier One Rd., Stevensville, MD 21666 ~21.35 miles southwest of Chestertown
  • High end Suburban property
  • Check in time: 4:00 PM
From$162
Very Good 4.5 /5Read Reviews CallBookMore Details
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