Chestertown, MD Hotels & Motels | HotelGuides.com
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Hotels in or near Chestertown, Maryland


Chestertown is located on the Chesapeake Bay in northeastern Maryland, 50 miles northeast of downtown Annapolis. The hotels in Chestertown are located off MD 213. The closest city with additional hotels is 28 miles south in Grasonville.

Map of Chestertown Hotels
 

    Hotels in or near Chestertown

    Rates shown below are averages. Click See Rates to see rates for your dates.
  • Quality Suites Chestertown
    160 Scheeler Road, Chestertown, MD 21620

    From $72
    Enter Dates
    Quality Suites Chestertown

    Check In15 00
    Check Out11 00

    Rated Average
  • Midscale, smoke-free, all-suite hotel near Washington College
  • Heated indoor swimming pool
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking
  • Not pet friendly - no pets allowed.
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 134 reviews  Read Recent Reviews

  • Holiday Inn Express Hotel & Suites Chestertown
    150 Scheeler Road, Chestertown, MD 21620

    From $103
    Enter Dates
    Holiday Inn Express Hotel & Suites Chestertown

    Check In15 00
    Check Out11 00

    Rated Average
  • Midscale, smoke-free hotel near Washington College
  • Heated indoor swimming pool - exercise room
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking
  • Pet friendly hotel More >
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 180 reviews  Read Recent Reviews

  • 19 miles Quality Inn Grasonville
    101 VFW Avenue, Grasonville, MD 21638
    19 miles from Chestertown
    From $207
    Enter Dates
    Quality Inn Grasonville

    Check In15 00
    Check Out11 00

    Rated Average
  • Upper-midscale, smoke-free hotel
  • 2 miles southeast of Kent Narrows
  • Outdoor swimming pool open in summer
  • Free hot breakfast buffet
  • Free WiFi - truck parking
  • Free parking
  • Not pet friendly - no pets allowed.
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 160 reviews  Read Recent Reviews

  • 19 miles Holiday Inn Express Grasonville
    1020 Kent Narrows Road, Grasonville, MD 21638
    19 miles from Chestertown
    From $102
    Enter Dates
    Holiday Inn Express Grasonville

    Check In15 00
    Check Out11 00

    Rated High
  • Midscale, smoke-free, waterfront hotel
  • Near Wells Cove and US 50/US 301, Exit 42
  • Outdoor swimming pool open in summer
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking - truck parking
  • Not pet friendly - no pets allowed.
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 248 reviews  Read Recent Reviews

  • 19 miles Best Western Kent Narrows Inn Grasonville
    3101 Main Street, Grasonville, MD 21638
    19 miles from Chestertown
    From $229
    Enter Dates
    Best Western Kent Narrows Inn Grasonville

    Check In1600
    Check Out1100

    Rated Average
  • Midscale, smoke-free hotel
  • Near Wells Cove and US 50 at US 301, Exit 41
  • Heated indoor swimming pool - exercise room
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking - truck parking
  • Not pet friendly - no pets allowed.
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 650 reviews  Read Recent Reviews

  • 19 miles Hilton Garden Inn Kent Island Grasonville
    3206 Main Street, Grasonville, MD 21638
    19 miles from Chestertown
    From $138
    Enter Dates
    Hilton Garden Inn Kent Island Grasonville

    Check In15 00
    Check Out12 00

    Rated Very High
  • Upper-midscale hotel
  • Near Wells Cove and US 50/US 301, Exit 42
  • Heated indoor swimming pool - exercise room
  • Free WiFi
  • Free parking
  • Not pet friendly - no pets allowed.
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 1000 reviews  Read Recent Reviews

  • 20 miles Home2 Suites by Hilton Aberdeen
    20 Newton Road, Aberdeen, MD 21001
    20 miles from Chestertown
    From $108
    Enter Dates
    Home2 Suites by Hilton Aberdeen

    Check In15 00
    Check Out12 00

    Rated High
  • Upscale, smoke-free, all-suite, highway hotel
  • 6 miles from Aberdeen Proving Ground
  • Indoor swimming pool - exercise rooom
  • Free continental breakfast
  • Free WiFi
  • Free parking
  • Pet friendly hotel More >
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 358 reviews  Read Recent Reviews

  • 20 miles SpringHill Suites by Marriott Middle River
    6110 Greenleigh Avenue, Middle River, MD 21220
    20 miles from Chestertown
    From $127
    Enter Dates
    SpringHill Suites by Marriott Middle River

    Check In1600
    Check Out1200

    Rated Very High
  • Midscale, smoke-free, all-suite hotel
  • Near Gunpowder Falls State Park
  • Indoor swimming pool - exercise room
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking
  • Not pet friendly - no pets allowed.
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 36 reviews  Read Recent Reviews

  • 21 miles Holiday Inn Belcamp
    1326 Policy Drive, Belcamp, MD 21017
    21 miles from Chestertown
    From $100
    Enter Dates
    Holiday Inn Belcamp

    Check In15 00
    Check Out11 00

    Rated Average
  • Upper-midscale, smoke-free hotel
  • 4 miles west of Aberdeen Proving Ground
  • Heated indoor swimming pool - exercise room
  • Free WiFi
  • Free parking
  • Not pet friendly - no pets allowed.
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 27 reviews  Read Recent Reviews

  • 21 miles Homewood Suites by Hilton Bel Air
    4170 Philadelphia Road, Bel Air, MD 21015
    21 miles from Chestertown
    From $102
    Enter Dates
    Homewood Suites by Hilton Bel Air

    Check In15 00
    Check Out12 00

    Rated High
  • Upscale, all-suite, extended-stay hotel
  • 3 miles southwest of Ripken Stadium
  • Heated indoor swimming pool - exercise room
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking - truck parking
  • Pet friendly hotel More >
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 428 reviews  Read Recent Reviews

  • 21 miles Comfort Inn & Suites Edgewood
    2112 A Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $73
    Enter Dates
    Comfort Inn & Suites Edgewood

    Check In15 00
    Check Out11 00

    Rated Average
    Midscale, smoke-free, interstate hotel
  • Near I-95, Exit 77
  • Heated indoor swimming pool - exercise room
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking
  • Not pet friendly - no pets allowed.
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 188 reviews  Read Recent Reviews

  • 21 miles Candlewood Suites Bel Air
    4216 Philadelphia Road, Bel Air, MD 21015
    21 miles from Chestertown
    From $106
    Enter Dates
    Candlewood Suites Bel Air

    Check In15 00
    Check Out11 00

    Rated High
  • Midscale, all-suite, extended-stay hotel
  • 6 miles West of Aberdeen Proving Ground
  • No swimming pool
  • Exercise room
  • Free WiFi
  • Free parking
  • Pet friendly hotel More >
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 127 reviews  Read Recent Reviews

  • 21 miles Holiday Inn Express Edgewood
    2118 Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $75
    Enter Dates
    Holiday Inn Express Edgewood

    Check In15 00
    Check Out11 00

    Rated High
  • Midscale, smoke-free, interstate hotel near I-95, Exit 77
  • Heated indoor swimming pool - exercise room
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking
  • Not pet friendly - no pets allowed.
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 113 reviews  Read Recent Reviews

  • 21 miles Red Roof Inn Edgewood
    2116 Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $56
    Enter Dates
    Red Roof Inn Edgewood

    Check In14 00
    Check Out11 00

    Rated Average
  • Cheap, interstate motel near I-95, Exit 77
  • No swimming pool
  • Free continental breakfast
  • Free WiFi
  • Free parking
  • Pet friendly hotel More >
    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 158 reviews  Read Recent Reviews

  • 21 miles Extended Stay America Hotel Bel Air
    1361 James Way, Bel Air, MD 21015
    21 miles from Chestertown
    From $95
    Enter Dates
    Extended Stay America Hotel Bel Air

    Check In15 00
    Check Out11 00

    Rated Average
  • Budget, all-suite, extended-stay hotel near I-95, Exit 80
  • No swimming pool
  • Free continental breakfast
  • Free WiFi
  • Free parking
  • Pet friendly hotel More >
    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 45 reviews  Read Recent Reviews

  • 21 miles Ramada Hotel & Conference Center Edgewood
    1700 Van Bibber Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $68
    Enter Dates
    Ramada Hotel & Conference Center Edgewood

    Check In1500
    Check Out1100

    Rated Average
  • Midscale, interstate motel near I-95, Exit 77
  • Outdoor swimming pool open in summer - exercise room
  • Free continental breakfast
  • Free WiFi
  • Free parking
  • Pet friendly motel More >
    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 352 reviews  Read Recent Reviews

  • 21 miles La Quinta Inn & Suites Edgewood
    2112-B Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $82
    Enter Dates
    La Quinta Inn & Suites Edgewood

    Check In15 00
    Check Out12 00

    Rated Very High
    Midscale, smoke-free, interstate hotel
  • Near I-95, Exit 77
  • No swimming pool
  • Exercise room
  • Free continental breakfast
  • Free WiFi
  • Free parking
  • Pet friendly hotel More >
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 455 reviews  Read Recent Reviews

  • 21 miles SpringHill Suites by Marriott Bel Air
    1420 Handlir Drive, Bel Air, MD 21015
    21 miles from Chestertown
    From $80
    Enter Dates
    SpringHill Suites by Marriott Bel Air

    Check In1600
    Check Out1100

    Rated High
  • Midscale, smoke-free, all-suite hotel
  • 3 miles southwest of Ripken Stadium
  • Heated indoor swimming pool - exercise room
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking
  • Not pet friendly - no pets allowed.
    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 185 reviews  Read Recent Reviews

  • 21 miles Country Inn & Suites by Radisson Bel Air
    1435 Handlir Drive, Bel Air, MD 21015
    21 miles from Chestertown
    From $99
    Enter Dates
    Country Inn & Suites by Radisson Bel Air

    Check In15 00
    Check Out12 00

    Rated Very High
  • Midscale hotel near I-95
  • 6 miles southwest of Ripken Stadium
  • Outdoor swimming pool - exercise room
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking
  • Not pet friendly - no pets allowed.
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 643 reviews  Read Recent Reviews

  • 21 miles Hampton Inn & Suites Edgewood
    2110 Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $89
    Enter Dates
    Hampton Inn & Suites Edgewood

    Check In15 00
    Check Out11 00

    Rated Very High
  • Midscale, smoke-free hotel near I-95 at MD 24
  • Heated indoor swimming pool - exercise room
  • Free hot breakfast buffet
  • Free WiFi
  • Free parking
  • Not pet friendly - no pets allowed.
    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 823 reviews  Read Recent Reviews

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Chestertown Info

Pet Friendly Hotels in or near Chestertown

Chestertown Group Hotel Rates

Map of Chestertown MD Hotels

Nearby Attractions


Hotels near Washington College   0.4 mile north
Hotels near Mount Harmon Plantation   14 miles NE
Hotels near Queenstown Premium Outlets   17 miles south
Hotels near Chesapeake College   18 miles south
Hotels near Aberdeen Proving Ground   19 miles north
Hotels near Elk Neck State Park   19 miles north
Hotels near Jetty Dock Bar   19 miles SW
Hotels near Aspen Wye River Conference Center   21 miles south
Hotels near Chesapeake Bay Beach Club   21 miles SW
Hotels near Bay Bridge MD   22 miles SW
Hotels near Sandy Point State Park   22 miles SW
Hotels near Perry Point VA Medical Center   23 miles north
Hotels near Anchor Inn   24 miles west
Hotels near White Marsh Mall   24 miles NW
Hotels near Triple Creek Winery   25 miles south
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Nearby Cities


Centreville MD Hotels   12 miles south
Queenstown MD Hotels   16 miles south
Grasonville MD Hotels   19 miles SW
Hartly DE Hotels   19 miles east
Edgewood MD Hotels   20 miles NW
Belcamp MD Hotels   20 miles NW
Riverside MD Hotels   20 miles NW
Edgemere MD Hotels   20 miles west
Abingdon MD Hotels   21 miles NW
Stevensville MD Hotels   21 miles SW
Aberdeen MD Hotels   21 miles north
Middle River MD Hotels   21 miles west
Joppa MD Hotels   22 miles NW
Greensboro MD Hotels   22 miles SE
Essex MD Hotels   23 miles west
How Do We Order Hotels?

On place pages like this, we order hotels from lowest cost to highest – except we list low-rated hotels at the bottom of the page.

Most of our competitors order these same hotels in other ways that make them more money.
How Do We Define Motel?

To us, motels are smaller lodgings that have rooms you can enter directly from the parking area.

At hotels, on the other hand, you can enter your room only through a hall inside the building.
Hotel Tips

Important Hotel Tips


Chestertown Hotels, Motels, Lodging, and Accommodations – Chestertown, Maryland MD, USA

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