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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
  • Low Cost Riverfront property
  • Check in: 2:00pm
  • Nice location
  • Oldest motel
Quality Suites in Chestertown 160 Scheeler Rd., Chestertown, MD 21620
  • Affordable Rural hotel
  • Hotel has 53 rooms
Holiday Inn Express & Suites Chestertown Md 150 Scheeler Rd., Chestertown, MD 21620
  • 3-star Suburban property
  • Fitness / Gym is on-site
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • Expensive Rural property
  • Hotel has 6 suites
Sleep Inn Grasonville 101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • Two star Resort property
  • Hotel has 59 rooms
Holiday Inn Express Annapolis East / Kent Island - Grasonville 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • Midscale Rural hotel
  • Hotel has 3 meeting rooms
From$180
Very Good 4.0 /5Read Reviews CallBookMore Details
Best Western Kent Narrows Inn - Grasonville 3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • Two-star Resort hotel
  • Fitness / Gym is on-site
  • Wet floor
  • Great restaurants nearby
Hilton Garden Inn Kent Island in Grasonville 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Mid-scale Riverfront property
  • Gym is available on property
  • Spacious rooms
  • Very friendly & efficient staffs there
From$139
Very Good 4.5 /5Recent Reviews CallBookMore Details
Home2 Suites by Hilton Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Three Star Suburban hotel
  • Hotel has 107 suites
From$104
Very Good 4.0 /5Reviews CallBookMore Details
Budget Inn of Aberdeen
+1-800-881-1523
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Low Cost Downtown property
  • Check in time: 12.00
  • Quite clean
  • Clean room
From$64
Very Good 4.5 /5Review Score CallBookMore Details
Arborview at Riverside in Liriope : 1307 Liriope Court 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • 4-star hotel
  • Hotel has 3 floors
Wingate by Wyndham in Belcamp 1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Affordable Suburban hotel
  • 3 meeting rooms in property
Holiday Inn 1326 Policy Dr., Belcamp, MD 21017 ~21.04 miles northwest of Chestertown
  • Mid-scale Suburban hotel
  • 107 sleeping rooms in hotel
Sleep Inn & Suites - Edgewood 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Cheap Suburban hotel
  • 84 rooms in property
  • Pool should be renewed
  • Most guests thought the tv was sub-standard
From$54
Very Good 4.0 /5Reviews CallBookMore Details
Motel 6 Edgewood in Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Low-priced Highway hotel
  • Check in: 3:00PM
Ramada Conference Center 1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • 2-star Suburban property
  • 152 sleeping rooms in hotel
  • Breakfast is mediocre
  • Could use a good cleaning
From$59
Average 3.0 /5Reviews CallBookMore Details
Candlewood Suites Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Economical Suburban property
  • Check-in: 3:00
  • Full size fridge
  • Room was nice and clean
Extended Stay America Baltimore Bel Air - Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Cheap Highway hotel
  • 101 rooms in hotel
Holiday Inn Express in Edgewood 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Affordable Suburban hotel
  • Check-in time: 3:00 pm
  • Big channel selection
  • Most guests thought the building was wonderful
From$119
Very Good 4.0 /5Latest Reviews CallBookMore Details
Red Roof Inn Edgewood in Edgewood 2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • Economy hotel
Comfort Inn & Suites Edgewood Aberdeen in Edgewood 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • 2-star Suburban hotel
  • Check in time: 3:00 PM
  • Clean linen
  • Quiet location
Homewood Suites by Hilton - Bel Air
+1-888-690-5247
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Check-in time: 3:00pm
  • Perfectly clean
  • Clean
From$159
Very Good 4.5 /5Review Score 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 rooms in property
  • Breakfast is mediocre
  • Comfort level is high
From$119
Very Good 4.0 /5Guest Reviews CallBookMore Details
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • 3 star Rural hotel
  • Gym is available on property
  • Tasty breakfast
  • Popular among families
The Inn at the Chesapeake Bay Beach Club & Spa in Stevensville 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 /5Latest Reviews CallBookMore Details
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