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Hotels and Motels in or near Chestertown, MD


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, MD Hotels and Motels
 
 Rates shown below are averages. Use Search above to see rates for your dates.
  • Red Roof Inn & Suites Chestertown

    160 Scheeler Road, Chestertown, MD 21620

    Enter Dates
    Red Roof Inn & Suites Chestertown

    Check In15 00
    Check Out11 00

    Rated Average
    • Cheap, smoke-free hotel
    • Near Washington College
    • 3 floors, 53 rooms and suites - elevator
    • Heated indoor swimming pool
    • Microwave and refrigerator in every room
    • Free WiFi
    • Free parking
  • Pet friendly hotel More >
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 143 reviews  Read Recent Reviews

  • Comfort Inn & Suites Chestertown

    150 Scheeler Road, Chestertown, MD 21620

    Enter Dates
    Comfort Inn & Suites Chestertown

    Check In15 00
    Check Out11 00

    Rated High
    • Midscale, smoke-free hotel
    • Near Washington College
    • 3 floors, 81 rooms and suites - elevator
    • Outdoor swimming pool open in summer - exercise room
    • Microwave and refrigerator in every 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 191 reviews  Read Recent Reviews

  • 19 miles Holiday Inn Express Grasonville

    1020 Kent Narrows Road, Grasonville, MD 21638
    19 miles to Chestertown

    Enter Dates
    Holiday Inn Express Grasonville

    Check In15 00
    Check Out11 00

    Rated High
    • Upper-midscale, smoke-free, waterfront hotel
    • Near Wells Cove and US 50/US 301, Exit 42
    • 3 floors, 75 rooms - elevator
    • Outdoor swimming pool open in summer
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking - truck parking
  • Not pet friendly - no pets allowed. - May 2021
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 266 reviews  Read Recent Reviews

  • 19 miles Best Western Kent Narrows Inn Grasonville

    3101 Main Street, Grasonville, MD 21638
    19 miles to Chestertown

    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 - limited truck parking
  • Pet friendly hotel More >
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 818 reviews  Read Recent Reviews

  • 19 miles Hyatt Place Hotel Kent Narrows & Marina Grasonville
    3028 Kent Narrow Way South, Grasonville, MD 21638
    19 miles to Chestertown

    Enter Dates
    Hyatt Place Hotel Kent Narrows & Marina Grasonville

    Check In16 00
    Check Out11 00

    • Upscale, smoke-free, waterfront hotel & marina
    • Located in historic Fisherman's Village
    • 4 floors, 120 rooms
    • Heated indoor swimming pool - 24-hour exercise room
    • Restaurant - lounge
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Pet friendly hotel More >

  • 19 miles Hilton Garden Inn Kent Island Grasonville

    3206 Main Street, Grasonville, MD 21638
    19 miles to Chestertown

    Enter Dates
    Hilton Garden Inn Kent Island Grasonville

    Check In15 00
    Check Out12 00

    Rated High
    • Upscale, smoke-free hotel
    • Near Wells Cove and US 50/US 301, Exit 42
    • 5 floors, 90 rooms
    • Heated indoor swimming pool - exercise room
    • Restaurant - lounge - room service
    • Restaurant open for breakfast and dinner only
    • Microwave and refrigerator in every room
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Sep 2015
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 1070 reviews  Read Recent Reviews

  • 20 miles Home2 Suites by Hilton Aberdeen

    20 Newton Road, Aberdeen, MD 21001
    20 miles to Chestertown

    Enter Dates
    Home2 Suites by Hilton Aberdeen

    Check In15 00
    Check Out12 00

    Rated High
    • Upper-midscale, smoke-free, all-suite, extended-stay hotel
    • 6 miles from Aberdeen Proving Ground
    • 5 floors, 107 studio and one-bedroom suites
    • Indoor swimming pool - exercise rooom
    • Kitchen in every suite
    • 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 389 reviews  Read Recent Reviews

  • 20 miles SpringHill Suites by Marriott Middle River

    6110 Greenleigh Avenue, Middle River, MD 21220
    20 miles to Chestertown

    Enter Dates
    SpringHill Suites by Marriott Middle River

    Check In1600
    Check Out1200

    Rated High
    • Upscale, smoke-free, all-suite hotel
    • Near Gunpowder Falls State Park
    • 4 floors, 120 studio suites
    • Indoor swimming pool - exercise room
    • Microwave and refrigerator in every suite
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Jul 2018
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 49 reviews  Read Recent Reviews

  • 21 miles Holiday Inn Belcamp - I-95, Exit 80

    1326 Policy Drive, I-95, Exit 80, Belcamp, MD 21017
    21 miles to Chestertown

    Enter Dates
    Holiday Inn Belcamp - I-95, Exit 80

    Check In15 00
    Check Out11 00

    Rated Average
    • Upper-midscale, smoke-free hotel
    • 4 miles west of Aberdeen Proving Ground
    • 3 floors, 107 rooms - elevator
    • Heated indoor swimming pool - exercise room
    • Restaurant - lounge
    • Restaurant open for breakfast and dinner only
    • Microwave and refrigerator in every room
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Nov 2017
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 30 reviews  Read Recent Reviews

  • 21 miles Ramada Hotel & Conference Center Edgewood - I-95, Exit 77

    1700 Van Bibber Road, I-95, Exit 77, Edgewood, MD 21040
    21 miles to Chestertown

    Enter Dates
    Ramada Hotel & Conference Center Edgewood - I-95, Exit 77

    Check In1500
    Check Out1100

    Rated Average
    • Midscale, interstate motel near I-95, Exit 77
    • 2 floors, 152 rooms - no elevator
    • Some smoking rooms
    • Outdoor swimming pool open in summer
    • Exercise room
    • Microwave and refrigerator in every room
    • Free continental breakfast
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Dec 2021
  • TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 362 reviews  Read Recent Reviews

  • 21 miles Quality Inn & Suites Edgewood - I-95, Exit 77

    2112-A Emmorton Park Road, I-95, Exit 77, Edgewood, MD 21040
    21 miles to Chestertown

    Enter Dates
    Quality Inn & Suites Edgewood - I-95, Exit 77

    Check In15 00
    Check Out11 00

    Rated High
    • Midscale, smoke-free, interstate hotel
    • Near I-95, Exit 77
    • 2 floors, 104 rooms and suites - elevator
    • Heated indoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Jan 2020
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 198 reviews  Read Recent Reviews

  • 21 miles Holiday Inn Express Edgewood - I-95, Exit 77

    2118 Emmorton Park Road, I-95, Exit 77, Edgewood, MD 21040
    21 miles to Chestertown

    Enter Dates
    Holiday Inn Express Edgewood - I-95, Exit 77

    Check In15 00
    Check Out11 00

    Rated High
    • Upper-midscale, smoke-free, interstate hotel
    • Near I-95, Exit 77
    • 3 floors, 80 rooms and suites - elevator
    • Heated indoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Apr 2021
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 118 reviews  Read Recent Reviews

  • 21 miles TownePlace Suites by Marriott Belcamp - I-95, Exit 80
    1357 Belcamp Road, I-95, Exit 80, Belcamp, MD 21017
    21 miles to Chestertown

    Enter Dates
    TownePlace Suites by Marriott Belcamp - I-95, Exit 80

    Check In1500
    Check Out1200

    • Midscale, smoke-free, all-suite, extended-stay hotel
    • 10 miles from Aberdeen Proving Ground
    • 4 floors, 96 suites
    • Indoor swimming pool - 24-hour exercise room
    • Kitchen in every suite
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Pet friendly hotel More >

  • 21 miles Red Roof Inn Edgewood - I-95, Exit 77

    2116 Emmorton Park Road, I-95, Exit 77, Edgewood, MD 21040
    21 miles to Chestertown

    Enter Dates
    Red Roof Inn Edgewood - I-95, Exit 77

    Check In14 00
    Check Out11 00

    Rated Average
    • Cheap, interstate motel near I-95, Exit 77
    • 2 floors, 72 rooms - no elevator
    • Some smoking rooms
    • No swimming pool
    • Microwave and refrigerator in every room
    • Free continental breakfast
    • Free WiFi
    • Free parking
  • Pet friendly motel More >
  • TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 168 reviews  Read Recent Reviews

  • 21 miles Extended Stay America Suites Bel Air - I-95, Exit 80

    1361 James Way, I-95, Exit 80, Bel Air, MD 21015
    21 miles to Chestertown

    Enter Dates
    Extended Stay America Suites Bel Air - I-95, Exit 80

    Check In15 00
    Check Out11 00

    Rated High
    • Budget, smoke-free, all-suite, extended-stay hotel
    • Near I-95, Exit 80
    • 3 floors, 101 suites - elevator
    • No swimming pool
    • Kitchen in every suite
    • Free continental breakfast
    • Free WiFi
    • Free parking
  • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 74 reviews  Read Recent Reviews

  • 21 miles Country Inn & Suites by Radisson Bel Air - I-95, Exit 80

    1435 Handlir Drive, I-95, Exit 80, Bel Air, MD 21015
    21 miles to Chestertown

    Enter Dates
    Country Inn & Suites by Radisson Bel Air - I-95, Exit 80

    Check In15 00
    Check Out12 00

    Rated Very High
    • Upper-midscale, smoke-free hotel near I-95
    • 6 miles southwest of Ripken Stadium
    • 3 floors, 81 rooms and suites - elevator
    • Outdoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Sep 2015
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 680 reviews  Read Recent Reviews

  • 21 miles La Quinta Inn & Suites Edgewood - I-95, Exit 77

    2112-B Emmorton Park Road, I-95, Exit 77, Edgewood, MD 21040
    21 miles to Chestertown

    Enter Dates
    La Quinta Inn & Suites Edgewood - I-95, Exit 77

    Check In15 00
    Check Out11 00

    Rated High
    • Midscale, smoke-free, interstate hotel
    • Near I-95, Exit 77
    • 3 floors, 64 rooms and suites - elevator
    • No swimming pool
    • Exercise room
    • Microwave and refrigerator in every room
    • 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 482 reviews  Read Recent Reviews

  • 21 miles Hilton Garden Inn Bel Air - I-95, Exit 80
    4160 Philadelphia Road, I-95, Exit 80, Bel Air, MD 21015
    21 miles to Chestertown

    Enter Dates
    Hilton Garden Inn Bel Air - I-95, Exit 80

    Check In15 00
    Check Out11 00

    • Upscale, smoke-free, interstate hotel
    • Near I-95, Exit 80
    • 4 floors, 102 rooms and suites
    • Heated indoor swimming pool - exercise room
    • Restaurant - lounge - room service
    • Restaurant open for dinner only
    • Free WiFi
    • Free parking
  • Pet friendly hotel More >

  • 21 miles Homewood Suites by Hilton Bel Air - I-95, Exit 80

    4170 Philadelphia Road, I-95, Exit 80, Bel Air, MD 21015
    21 miles to Chestertown

    Enter Dates
    Homewood Suites by Hilton Bel Air - I-95, Exit 80

    Check In15 00
    Check Out12 00

    Rated High
    • Upscale, smoke-free, all-suite, extended-stay hotel
    • 3 miles southwest of Ripken Stadium
    • 5 floors, 92 suites
    • Heated indoor swimming pool - exercise room
    • Kitchen in every suite
    • 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 465 reviews  Read Recent Reviews

  • 21 miles SpringHill Suites by Marriott Bel Air - I-95, Exit 80

    1420 Handlir Drive, I-95, Exit 80, Bel Air, MD 21015
    21 miles to Chestertown

    Enter Dates
    SpringHill Suites by Marriott Bel Air - I-95, Exit 80

    Check In1600
    Check Out1100

    Rated High
    • Upscale, smoke-free, all-suite hotel
    • 3 miles southwest of Ripken Stadium
    • 3 floors, 119 studio suites - elevator
    • Heated indoor swimming pool - exercise room
    • Microwave and refrigerator in every suite
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Sep 2015
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 193 reviews  Read Recent Reviews

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Chestertown Info

Chestertown Group Hotel Rates

Hotels near Me

Nearby Attractions


Hotels near Washington College   0.4 mile north
Hotels near Mount Harmon Plantation   14 miles NE
Hotels near Chesapeake College   18 miles south
Hotels near Tuckahoe State Park   18 miles SE
Hotels near Red Eye's Dock Bar   19 miles SW
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 Celebrations at the Bay   21 miles west
Hotels near Kurtz's Beach   21 miles west
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 Ripken Experience   23 miles north
Hotels near Sandy Cove Ministries   23 miles north

Nearby Cities


Georgetown MD Hotels   7 miles west
Centreville MD Hotels   12 miles south
Queenstown MD Hotels   16 miles south
Grasonville MD Hotels   19 miles SW
Kent Narrows MD Hotels   19 miles SW
Belcamp 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
Bel Air MD Hotels   21 miles NW
Middle River MD Hotels   21 miles west
Greensboro MD Hotels   22 miles SE
Essex MD Hotels   23 miles west
Havre de Grace MD Hotels   23 miles north
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How Do We Define Motel?

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At hotels, on the other hand, you can enter your room only through a hall inside the building.
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  5. The earlier in the afternoon you check into a hotel, the more likely you will get a room or suite that matches your preferences.



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

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