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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 - Chestertown 609 Washington Ave., Chestertown, MD 21620
  • 2-star Riverfront hotel
  • 3 suites in property
  • Most guests thought it was rather dirty
  • Spacious rooms
Comfort Suites
+1-800-230-4134
160 Scheeler Rd., Chestertown, MD 21620
  • Mid-scale Rural hotel
  • Hotel has 53 suites
  • Breakfast is average
  • Check in was quick
Holiday Inn Express & Suites Chestertown Md 150 Scheeler Rd., Chestertown, MD 21620
  • 3 star Suburban property
  • 3 floors in property
From$162
Very Good 4.0 /5Latest Reviews Call
Brampton Inn 25227 Chestertown Rd., Chestertown, MD 21620
  • Expensive Rural hotel
  • 13 sleeping rooms in hotel
Holiday Inn Express Kent Island / Annapolis East
+1-888-305-3366
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Mid-scale Rural hotel
  • 3 floors in hotel
  • Very good family hotel
  • Most guests enjoyed the fish/seafood dishes
Best Western Kent Narrows Inn : 3101 Main St. 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Economical Resort hotel
  • Fitness + Health Center
  • Friendly service
  • Great breakfast
Hilton Garden Inn Kent Island : 3206 Main St. 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • 3-star Riverfront property
  • Check in time: 03:00PM
  • Acceptable breakfast prices
  • Great amenities
From$124
Very Good 4.5 /5Read Reviews Call
Sleep Inn Grasonville Md.
+1-800-997-5149
101 V.f.w Ave., Grasonville, MD 21638 ~19.69 miles south of Chestertown
  • Two star Resort hotel
  • Hotel has 2 floors
  • All guests said it was a stylish hotel
  • Most guests complained about the bathroom
Home2 Suites by Hilton Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Three Star Suburban property
  • Hotel has an eco-friendly policy See more
From$99
Very Good 4.0 /5Reviews Call
Budget Inn of Aberdeen in Aberdeen
+1-800-230-4134
1112 South Philadelphia Blvd., Aberdeen, MD 21001 ~20.62 miles north of Chestertown
  • Two-star Downtown hotel
  • Hotel has 25 rooms
  • Rooms are ok
  • Comfort level is high
From$64
Very Good 4.5 /5Read Reviews Call
Arborview at Riverside in Liriope - Belcamp 1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • 4 star property
  • Check-in: 4:00 p.m.
Wingate by Wyndham - Belcamp 1326 Poilicy Dr., Belcamp, MD 21017 Website ~20.99 miles northwest of Chestertown
  • Midscale Suburban property
  • Hotel has 7 suites
Sleep Inn & Suites 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • 2 star Suburban property
  • Fitness center on property
  • Lots of stores for shopping
  • Bathroom needs cleaning
Motel 6 Edgewood : 1709 Edgewood Rd. 1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Cheap Highway property
  • 2 conference rooms in property
The Inn at the Chesapeake Bay Beach Club : 180 Pier One Rd. 180 Pier One Rd., Stevensville, MD 21666 ~21.19 miles southwest of Chestertown
  • Expensive Resort property
  • Fitness center on property
From$162
Very Good 4.5 /5Guest Reviews Call
Ramada Conference Center - Edgewood
+1-800-997-5149
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.20 miles northwest of Chestertown
  • 2-star Suburban hotel
  • Free breakfast
  • Amenities are not the best
  • Dated interior
Candlewood Suites Bel Air in Bel Air 4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Two star Suburban property
  • Fitness center on property
  • Comfortable beds
  • Most guests thought the cleanliness of the hotel was average
Extended Stay America Baltimore Bel Air 1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Two-star Highway property
  • Hotel has 3 floors
Holiday Inn Express : 2118 Emmorton Park Rd. 2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • 3-star Suburban hotel
  • Gym is available on property
  • Clean rooms
  • Outstanding friendly personnel at front desk
From$119
Very Good 4.0 /5Review Score Call
Comfort Inn & Suites Edgewood Aberdeen Bel Air : 2112a Emmorton Park Rd. 2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Two-star Suburban property
  • Check-in: 3:00 PM
  • Most guests said the reception staff was great
  • WiFi system needs upgrading
Homewood Suites by Hilton
+1-888-305-3366
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Midscale Suburban property
  • Check-in: 3:00pm
  • Grocery store just down the street
  • Quick check-in
From$159
Very Good 4.5 /5Review Score Call
Springhill Suites by Marriott Edgewood Aberdeen 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Affordable Highway hotel
  • 119 rooms in hotel
  • Comfort level is high
  • Fantastic service
From$96
Very Good 4.0 /5Reviews Call
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 property
  • Terrific location
  • Almost all guests liked the big bathroom
Hampton Inn & Suites Edgewood / Aberdeen South - Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Mid-scale Suburban property
  • Hotel has 134 rooms
  • Most guests thought rooms were spacious
  • Excellent pool
La Quinta Inn & Suites Edgewood Aberdeen Bel Air in Edgewood 2112b Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Midscale Suburban property
  • Hotel has 3 floors
  • Average comfort
  • Comfortable
From$65
Very Good 4.5 /5Read Reviews Call
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