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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
  • Low-priced Riverfront hotel
  • 3 suites in property
  • Hotel facilities could use a good clean
  • Rooms in need of an update
Quality Suites 160 Scheeler Rd., Chestertown, MD 21620
  • Three Star Rural hotel
  • Free breakfast
Holiday Inn Express & Suites Chestertown Md 150 Scheeler Rd., Chestertown, MD 21620
  • Affordable Suburban property
  • Free comp. breakfast
Brampton Inn - Chestertown 25227 Chestertown Rd., Chestertown, MD 21620
  • 4-star Rural property
  • 3 floors in property
Sleep Inn Grasonville - Grasonville 101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • Economical Resort hotel
  • Check in time: 11:00
Holiday Inn Express Annapolis East / Kent Island - Grasonville 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • Midscale Rural property
  • Hotel has 3 meeting rooms
From$180
Very Good 4.0 /5Review Score CallBookMore Details
Best Western Kent Narrows Inn : 3101 Main St. 3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • Cheap Resort property
  • Check in: 4:00 PM
  • Great breakfast and clean rooms with friendly staff
  • Friendly front desk
Hilton Garden Inn Kent Island in Grasonville 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Three Star Riverfront property
  • 90 rooms in property
  • Excellent customer service
  • Close to restaurants and bars
From$136
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
  • Three Star Suburban property
  • Comp. Breakfast
From$104
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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
  • 4 suites in hotel
  • Good budget hotel
  • Service and overall comfort levels are top notch
From$64
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Arborview at Riverside in Liriope in Belcamp 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • High end hotel
Wingate by Wyndham 1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Midscale Suburban property
  • Check-in time: 3pm
Holiday Inn Belcamp Aberdeen Area 1326 Policy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • 3-star Suburban hotel
  • Check in time: 3pm
Sleep Inn & Suites : 1807 Edgewood Rd. 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Low Cost Suburban property
  • 16 suites in property
  • No working phone in the pool area
  • Dirty pool, said 89%
Motel 6 Edgewood - Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • 2-star Highway hotel
  • Access to gym on-site
Ramada Conference Center : 1700 Van Bibber Rd. 1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Economical Suburban property
  • 4 meeting rooms in hotel
  • About half of guests said rooms were dirty
  • More comfort would be nice
Candlewood Suites Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Economical Suburban property
  • 3 floors in hotel
  • Pleased with the comfort
  • Great team
Extended Stay America Baltimore Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Low priced Highway property
  • 101 rooms in hotel
Holiday Inn Express : 2118 Emmorton Park Rd. 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Midscale Suburban property
  • 3 floors in property
  • Staff was friendly and very accommodating
  • Fantastic service
From$119
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Red Roof Inn Edgewood in Edgewood 2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • Economical hotel
Comfort Inn & Suites Edgewood Aberdeen 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Inexpensive Suburban property
  • 2 floors in hotel
  • Room cleanliness is acceptable
  • Most guests were happy with the price of the breakfast
Homewood Suites by Hilton
+1-888-690-5247
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Three Star Suburban property
  • Check in time: 3:00pm
  • Nice breakfast arrangement
  • Bathroom could be optimized
From$159
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Springhill Suites by Marriott Edgewood Aberdeen : 1420 Handlir Dr. 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • 3 star Highway property
  • Gym is available on property
  • Bed was comfortable
  • Very good hotel
From$106
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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
  • Mid-scale Rural hotel
  • Fitness center on property
  • Clean rooms
  • Delicious food
From$79
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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
  • Hotel has 12 suites
From$162
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