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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., Chestertown, MD 21620
  • Low priced Riverfront hotel
  • Hotel has 27 rooms
  • Facility old
  • Room needs to be redecorated
Quality Suites 160 Scheeler Rd., Chestertown, MD 21620
  • Three Star Rural property
  • 53 rooms in property
Holiday Inn Express & Suites Chestertown Md 150 Scheeler Rd., Chestertown, MD 21620
  • Midscale Suburban property
  • Hotel has 3 floors
From$95
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • 4 star Rural hotel
  • Hotel has 3 floors
Sleep Inn Grasonville in Grasonville
+1-866-221-8581
101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • Low Cost Resort hotel
  • 59 rooms in hotel
From$60
Average 3.5 /5 Reviews Call BookMore Details
Holiday Inn Express Annapolis East / Kent Island - Grasonville 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • 3 star Rural hotel
  • 3 floors in hotel
From$180
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Best Western Kent Narrows Inn : 3101 Main St. 3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • Economy Resort property
  • Check-in time: 3:00 PM
  • Food is to die for
  • High price
From$67
Average 3.5 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn Kent Island - Grasonville 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Midscale Riverfront hotel
  • Check in time: 03:00PM
  • Homey feeling
  • Reception is all right
From$124
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Home2 Suites by Hilton Aberdeen in Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Mid-scale Suburban property
  • 5 floors in hotel
From$99
Very Good 4.0 /5 Recent Reviews Call BookMore 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
  • Free Wifi
  • Service and overall comfort levels are top notch
From$64
Very Good 4.5 /5 Read Reviews Call BookMore Details
Arborview at Riverside in Liriope in Belcamp 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • 4-star hotel
  • 3 floors in property
Wingate by Wyndham 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • Three Star Suburban property
  • Fitness center on property
From$69
Average 3.5 /5 Guest Reviews Call BookMore Details
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Low Cost Suburban property
  • Gym / Fitness Center Available
  • Most guests complained about the bathroom
  • Shower was ok
From$65
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Motel 6 Edgewood 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Economical Highway hotel
  • 134 rooms in hotel
Ramada Conference Center - Edgewood 1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Economical Suburban property
  • Check in time: 3:00pm
  • Stale cereal
  • AC worked great
From$59
Average 3.0 /5 Read Reviews Call BookMore Details
Candlewood Suites Bel Air in Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Low Cost Suburban hotel
  • 3 floors in property
  • Very good hotel
  • Room was nice and clean
From$65
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Extended Stay America Baltimore Bel Air : 1361 James Way 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Low-priced Highway property
  • 101 rooms in hotel
From$104
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express : 2118 Emmorton Park Rd. 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Mid-scale Suburban hotel
  • Fitness + Health Center
  • Very good family hotel
  • Great restaurants
From$119
Very Good 4.0 /5 Review Score Call BookMore Details
Red Roof Inn Edgewood in Edgewood 2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • Low Cost property
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
Comfort Inn & Suites Edgewood Aberdeen Bel Air 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Economy Suburban hotel
  • Hotel has 20 suites
  • Staff was amazing
  • Bathroom is relatively clean
From$57
Very Good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton - Bel Air
+1-888-690-5281
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Mid-scale Suburban property
  • 92 suites in hotel
  • Nice location
  • Rather comfortable
From$159
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Springhill Suites by Marriott Edgewood Aberdeen 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Three Star Highway hotel
  • Hotel has 3 floors
  • Dry cereals
  • Clean room
From$96
Very Good 4.0 /5 Review Score Call BookMore 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
  • 3 star Rural hotel
  • Access to gym on-site
  • Fantastic service
  • Great location
From$75
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
The Inn at the Chesapeake Bay Beach Club & Spa 180 Pier One Rd., Stevensville, MD 21666 ~21.35 miles southwest of Chestertown
  • Expensive Suburban property
  • Gym is available on property
From$162
Very Good 4.5 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Edgewood / Aberdeen South 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Affordable Suburban property
  • Free complimentary breakfast
  • Updated decor
  • Clean rooms
From$89
Very Good 4.5 /5 Guest Reviews Call BookMore Details
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