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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
  • Hotel has 3 suites
  • Most guests thought they were poorly maintained
  • About half of guests didn't like the uncomfortable beds
Quality Suites : 160 Scheeler Rd. 160 Scheeler Rd., Chestertown, MD 21620
  • 3 star Rural hotel
  • 53 rooms in hotel
Holiday Inn Express & Suites Chestertown Md 150 Scheeler Rd., Chestertown, MD 21620
  • Affordable Suburban hotel
  • Free breakfast
From$95
Very Good 4.0 /5Review Score Call
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • High-end Rural property
  • Check in time: 3:00PM
Sleep Inn in Grasonville
+1-888-305-3366
101 Vfw Ave., Grasonville, MD 21638 ~18.60 miles southwest of Chestertown
  • Cheap Resort property
  • Free comp. breakfast
Holiday Inn Express Annapolis East / Kent Island - Grasonville 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • Three Star Rural hotel
  • Free breakfast
From$180
Very Good 4.0 /5Recent Reviews Call
Best Western Kent Narrows Inn - Grasonville 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Low priced Resort hotel
  • Fitness center on property
  • Fresh seafood
  • Clean rooms
Hilton Garden Inn Kent Island : 3206 Main St. 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • 3 star Riverfront hotel
  • Check-in time: 03:00PM
  • Every guests reviewed enjoyed the friendly atmosphere
  • Roomy suite
From$124
Very Good 4.5 /5Recent Reviews Call
Home2 Suites by Hilton Aberdeen : 20 Newton Rd. 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • 3-star Suburban property
  • Hotel has an eco-friendly policy See more
Budget Inn of Aberdeen in Aberdeen
+1-800-230-4134
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • 2-star Downtown hotel
  • Check in time: 12.00
  • World class service
  • TV didn't work
Arborview at Riverside in Liriope - Belcamp 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • Four-star property
Wingate by Wyndham in Belcamp 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • Affordable Suburban hotel
  • 7 suites in hotel
Sleep Inn & Suites - Edgewood 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Low priced Suburban property
  • 16 suites in property
  • Most guests thought the shower was ok
  • New hotel/rooms
From$65
Very Good 4.0 /5Review Score Call
Motel 6 Edgewood - Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Inexpensive Highway property
  • 22 suites in property
Ramada Conference Center - Edgewood 1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • 2-star Suburban property
  • Fitness / Gym is on-site
  • Amenities are not the best
  • Hotel could use some updating
Candlewood Suites Bel Air : 4216 Philadelphia Rd. 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Cheap Suburban property
  • Hotel has an eco-friendly policy See policy
  • Very good hotel
  • Clean room
Extended Stay America Baltimore Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • 2 star Highway hotel
  • Check in time: 3:00pm
Holiday Inn Express : 2118 Emmorton Park Rd. 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Mid-scale Suburban hotel
  • Gym / Fitness Center Available
  • Great nights sleep
  • Generally very clean
From$119
Very Good 4.0 /5Review Score Call
Comfort Inn & Suites Edgewood Aberdeen Bel Air in Edgewood 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Low Cost Suburban property
  • 20 suites in property
  • Dated rooms
  • Comfort level is high
From$57
Very Good 4.5 /5Reviews Call
Homewood Suites by Hilton in Bel Air
+1-888-690-5247
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Mid-scale Suburban hotel
  • Fitness / Gym is on-site
  • Perfectly clean
  • Pool is below average
From$159
Very Good 4.5 /5Recent Reviews Call
Springhill Suites by Marriott Edgewood Aberdeen : 1420 Handlir Dr. 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Mid-scale Highway property
  • Check in: 3:00pm
  • Popular among business travelers
  • Breakfast was good
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 : 1435 Handlir Dr. 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Affordable Rural property
  • 81 rooms in hotel
  • All guests were happy with the price of the breakfast
  • All guests thought it was a great value
From$75
Very Good 4.5 /5Review Score Call
The Inn at the Chesapeake Bay Beach Club & Spa 180 Pier One Rd., Stevensville, MD 21666 ~21.35 miles southwest of Chestertown
  • High end Suburban property
  • Fitness + Health Center
From$162
Very Good 4.5 /5Recent Reviews Call
Hampton Inn & Suites Edgewood / Aberdeen South in Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Mid-scale Suburban property
  • Check in: 12:00 PM
  • Comfort level is high
  • Pool area comfortable
From$89
Very Good 4.5 /5Read Reviews Call
La Quinta Inn & Suites Edgewood Aberdeen Bel Air - Edgewood 2112b Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Three Star Suburban hotel
  • Comp. Breakfast
  • Regular internet service
  • Room free of charge
From$65
Very Good 4.5 /5Review Score Call
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