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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
  • Two star Riverfront property
  • 27 sleeping rooms in hotel
  • Most guests thought they were poorly maintained
  • Most guests said rooms were dirty
Holiday Inn Expres & Suites in Chestertown 150 Scheeler Rd., Chestertown, MD 21620
  • Mid-scale Suburban property
  • Check in time: 3:00pm
Quality Suites - Chestertown 160 Scheeler Rd., Chestertown, MD 21620
  • 3 star Rural hotel
  • Hotel has 53 suites
Brampton Inn : 25227 Chestertown Rd. 25227 Chestertown Rd., Chestertown, MD 21620
  • 4-star Rural property
  • Hotel has an eco-friendly policy See policy
Sleep Inn Grasonville in Grasonville 101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • Cheap Resort hotel
  • Free breakfast available
From$74
Average 3.5 /5Reviews CallBookMore Details
Holiday Inn Express Annapolis East / Kent Island in Grasonville 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • 3-star Rural hotel
  • 3 conference rooms in property
From$180
Very Good 4.0 /5Review Score CallBookMore Details
Best Western Kent Narrows Inn in Grasonville 3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • Cheap Resort hotel
  • Check-in: 4:00 PM
  • Fresh seafood
  • Clean towels
Hilton Garden Inn Kent Island in Grasonville 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Mid-scale Riverfront hotel
  • 90 rooms in hotel
  • Super friendly and accommodating staff
  • Nice balcony
From$142
Very Good 4.5 /5Review Score CallBookMore Details
Home2 Suites by Hilton Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Midscale Suburban property
  • Hotel has an eco-friendly policy Learn more
From$102
Very Good 4.0 /5Guest Reviews CallBookMore Details
Budget Inn of Aberdeen
+1-800-881-1523
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • 2 star Downtown property
  • Check-in time: 12.00
  • Good budget hotel
  • Decent vibe
Springhill Suites White Marsh 6110 Greenleigh Ave., Middle River, MD 21220 ~20.75 miles northwest of Chestertown
  • Mid-scale Suburban property
  • 120 suites in hotel
From$104
Very Good 4.5 /5Guest Reviews CallBookMore Details
Arborview at Riverside in Liriope 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • High end property
  • 3 floors in property
Wingate by Wyndham - Belcamp 1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Three Star Suburban property
  • 3 conference rooms in property
Holiday Inn Belcamp Aberdeen Area 1326 Policy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Fitness center on property
From$74
Average 3.0 /5Reviews CallBookMore Details
Americas Best Value Inn & Suites Aberdeen : 424 South Philadelphia Blvd. 424 South Philadelphia Blvd., Aberdeen, MD 21001 ~21.04 miles north of Chestertown
  • Economy hotel
  • Hotel has 40 rooms
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 Website ~21.07 miles northwest of Chestertown
  • 3 star Suburban property
  • 16 suites in property
  • World class service
  • Bathroom could be optimized
From$54
Very Good 4.0 /5Review Score CallBookMore Details
Motel 6 Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Low-priced Highway hotel
  • 22 suites in property
Ramada Conference Center : 1700 Van Bibber Rd. 1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Low priced Suburban property
  • Check-in: 3:00pm
  • Ideal location
  • About half of guests said rooms were dirty
From$59
Average 3.0 /5Reviews CallBookMore Details
Candlewood Suites Bel Air in Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Low-priced Suburban property
  • Access to gym on-site
  • Clean Rooms
  • Clean room
Extended Stay America Baltimore Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Low Cost Highway hotel
  • 101 suites in hotel
Holiday Inn Express in Edgewood 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Midscale Suburban property
  • Hotel has 92 rooms
  • Room is all right
  • Most guests thought the building was wonderful
From$119
Very Good 4.0 /5Review Score CallBookMore Details
Red Roof Inn Edgewood : 2116 Emmorton Park Rd. 2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • 2-star property
  • 2 floors in hotel
Comfort Inn & Suites Edgewood Aberdeen 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • 2-star Suburban hotel
  • Hotel has 20 suites
  • Room is all right
  • Great location
Homewood Suites by Hilton : 4170 Philadelphia Rd.
+1-800-881-1523
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Mid-scale Suburban property
  • Access to gym on-site
  • Without noise
  • Great room
From$159
Very Good 4.5 /5Recent Reviews CallBookMore Details
Springhill Suites by Marriott Edgewood Aberdeen 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • 3 star Highway property
  • 119 suites in hotel
  • Separate living area
  • Every guests reviewed found the staff to be very friendly
From$106
Very Good 4.0 /5Reviews CallBookMore Details
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