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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 - Chestertown 609 Washington Ave., Chestertown, MD 21620
  • Economical Riverfront property
  • Check-in: 2:00pm
  • Most guests complained about the bathroom
  • Most guests thought the building wasn't nice
Quality Suites 160 Scheeler Rd., Chestertown, MD 21620
  • Affordable Rural property
  • Check in time: 11:00
Holiday Inn Express & Suites Chestertown Md 150 Scheeler Rd., Chestertown, MD 21620
  • Mid-scale Suburban hotel
  • 81 sleeping rooms in hotel
Brampton Inn : 25227 Chestertown Rd. 25227 Chestertown Rd., Chestertown, MD 21620
  • High-end Rural hotel
  • Hotel has 3 floors
Sleep Inn Grasonville in Grasonville 101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • Low Cost Resort hotel
  • Free comp. breakfast
Holiday Inn Express Annapolis East / Kent Island 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • 3 star Rural property
  • Check-in time: 3:00pm
From$180
Very Good 4.0 /5Latest Reviews CallBookMore Details
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • Cheap Resort property
  • Check in: 3:00 PM
  • Good service
  • Almost all guests thought the view was good
Hilton Garden Inn Kent Island in Grasonville 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • 3-star Riverfront property
  • 90 rooms in hotel
  • Excellent hotel
  • Nicely appointed room
From$134
Very Good 4.5 /5Recent Reviews CallBookMore Details
Home2 Suites by Hilton Aberdeen - Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Midscale Suburban hotel
  • Gym is available on property
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
  • Two star Downtown property
  • Check in: 12.00
  • Friendly staff
  • Vibe was decent
Arborview at Riverside in Liriope in Belcamp 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • High end property
  • 3 floors in property
Wingate by Wyndham in Belcamp 1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • 3-star Suburban hotel
  • Check-in time: 3pm
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • 2 star Suburban hotel
  • Free complimentary breakfast
  • New rooms
  • Most guests thought, the hotel was modern
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
  • Economical Highway hotel
  • Gym is available on property
Ramada Conference Center : 1700 Van Bibber Rd. 1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • 2-star Suburban property
  • 4 meeting rooms in hotel
  • Terrible amenities
  • Most guests complained about the bathroom
Candlewood Suites Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Cheap Suburban property
  • Hotel has a green policy See policy
  • Most guests said the reception staff was great
  • Pleased with the comfort
Extended Stay America Baltimore Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Low priced Highway property
  • Check in time: 3:00pm
From$104
Average 3.5 /5Reviews CallBookMore Details
Holiday Inn Express : 2118 Emmorton Park Rd. 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Midscale Suburban hotel
  • 6 suites in hotel
  • Room is all right
  • Excellent location
From$119
Very Good 4.0 /5Recent Reviews CallBookMore Details
Red Roof Inn Edgewood - Edgewood 2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • 2 star hotel
Comfort Inn & Suites Edgewood Aberdeen Bel Air 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Low Cost Suburban property
  • Check-in: 3:00 PM
  • Quite clean
  • Great location
From$57
Very Good 4.0 /5Reviews CallBookMore Details
Homewood Suites by Hilton
+1-888-690-5281
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Affordable Suburban property
  • Check in: 3:00pm
  • New shower towels
  • Tasty breakfast
From$159
Very Good 4.5 /5Hotel Reviews CallBookMore Details
Springhill Suites by Marriott Edgewood Aberdeen - Bel Air 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Affordable Highway property
  • Check in time: 3:00pm
  • Fantastic service
  • Breakfast was good
From$114
Very Good 4.0 /5Recent Reviews CallBookMore Details
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 - Bel Air 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Midscale Rural property
  • Fitness / Gym is on-site
  • Excellent value
  • World class service
From$75
Very Good 4.5 /5Review Score CallBookMore Details
The Inn at the Chesapeake Bay Beach Club & Spa 180 Pier One Rd., Stevensville, MD 21666 ~21.35 miles southwest of Chestertown
  • Four-star Suburban hotel
  • Gym / Fitness Center Available
From$162
Very Good 4.5 /5Hotel Reviews CallBookMore Details
Hampton Inn & Suites Edgewood / Aberdeen South : 2110 Emmorton Park Rd. 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Affordable Suburban property
  • Fitness center on property
  • Good location
  • Comfort level is high
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