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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
  • Cheap Riverfront hotel
  • 27 rooms in hotel
  • Most guests had problems with the shower
  • Staff rude
Quality Suites : 160 Scheeler Rd. 160 Scheeler Rd., Chestertown, MD 21620
  • 3 star Rural hotel
  • Free breakfast available
Holiday Inn Express & Suites Chestertown Md 150 Scheeler Rd., Chestertown, MD 21620
  • Midscale Suburban hotel
  • Check-in time: 3:00pm
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • 4-star Rural property
  • Check-in time: 3:00PM
Sleep Inn Grasonville - Grasonville
+1-866-221-8581
101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • Two-star Resort hotel
  • Check-in: 11:00
Holiday Inn Express Annapolis East / Kent Island 1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • Midscale Rural hotel
  • Hotel has 3 floors
From$180
Very Good 4.0 /5Recent Reviews CallBookMore Details
Best Western Kent Narrows Inn : 3101 Main St. 3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • Two-star Resort hotel
  • 4 floors in hotel
  • Breakfast is good
  • Comfortable beds
Hilton Garden Inn Kent Island 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Affordable Riverfront property
  • Check in time: 03:00PM
  • Awesome vibe
  • Great room
From$134
Very Good 4.5 /5Guest Reviews CallBookMore Details
Home2 Suites by Hilton Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Affordable Suburban property
  • 5 floors in property
From$104
Very Good 4.0 /5Recent Reviews CallBookMore Details
Budget Inn of Aberdeen : 1112 South Philadelphia Blvd.
+1-800-881-1523
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Inexpensive Downtown hotel
  • 4 suites in property
  • TV didn't work
  • Most guests said rooms were clean enough
Arborview at Riverside in Liriope 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • High end property
  • 3 floors in hotel
Wingate by Wyndham 1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Three Star Suburban hotel
  • 3 meeting rooms in property
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Cheap Suburban property
  • 3 floors in property
  • Most guests were happy with the price of the breakfast
  • New rooms
From$65
Very Good 4.0 /5Reviews CallBookMore Details
Motel 6 Edgewood : 1709 Edgewood Rd. 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Low Cost Highway hotel
  • 2 conference rooms in property
Ramada Conference Center in Edgewood 1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • Low priced Suburban property
  • Free complimentary breakfast
  • Most guests thought the building wasn't nice
  • Older building
Candlewood Suites Bel Air : 4216 Philadelphia Rd. 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Economical Suburban hotel
  • Check-in: 3:00
  • Fantastic service
  • Friendly staff
From$65
Very Good 4.0 /5Review Score CallBookMore Details
Extended Stay America Baltimore Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Low-priced Highway hotel
  • Hotel has 101 suites
Holiday Inn Express in Edgewood 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • 3-star Suburban property
  • 92 sleeping rooms in hotel
  • Breakfast is good
  • Coffee in lobby was available
From$119
Very Good 4.0 /5Reviews CallBookMore Details
Red Roof Inn Edgewood : 2116 Emmorton Park Rd. 2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • 2 star hotel
Comfort Inn & Suites Edgewood Aberdeen Bel Air in Edgewood 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • 2-star Suburban property
  • Hotel has 20 suites
  • Terrific location
  • Bathroom is relatively clean
Homewood Suites by Hilton
+1-888-690-5281
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Midscale Suburban hotel
  • 5 floors in hotel
  • Great reception
  • Nice location
From$159
Very Good 4.5 /5Latest Reviews CallBookMore Details
Springhill Suites by Marriott Edgewood Aberdeen 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • 3 star Highway hotel
  • Check-in time: 3:00pm
  • Comfort level is high
  • Breakfast was good
From$104
Very Good 4.0 /5Read Reviews CallBookMore Details
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 in Bel Air 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Midscale Rural property
  • Check-in time: 3pm
  • For only 67%, the noise level was all right
  • Clean bathrooms
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 hotel
  • Check-in time: 4:00 PM
From$162
Very Good 4.5 /5Review Score CallBookMore Details
Hampton Inn & Suites Edgewood / Aberdeen South 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Midscale Suburban hotel
  • Hotel has 34 suites
  • Rooms are great
  • Excellent amenities
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