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Hotel Guides > Maryland > Chestertown Hotels & Motels

Hotels in or near Chestertown, Maryland

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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.

We can also help you find hotels in Chestertown, New York.

Map of Chestertown Hotels

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    Hotels in or near Chestertown

    Rates shown below are estimates. Click See Rates for actual current rates.
  • Quality Suites
    160 Scheeler Road, Chestertown, MD 21620

    From $72
    Enter Dates
    Quality Suites Chestertown

    Check In1500
    Check Out1100

    Rated High
    Midscale, smoke-free, all-suite hotel near Washington College 3 floors, 53 studio suites - elevator
    Heated indoor swimming pool
    Free hot breakfast buffet
    Free Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Mar 2015

    Most Recent HotelGuides Review
    "The hotel was nice and clean, and the front desk clerk was pleasant and accommodating. I recommend staying here.2017-06-20"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 119 reviews  Read Recent Reviews

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

    From $136
    Enter Dates
    Holiday Inn Express Hotel & Suites Chestertown

    Check In15 00
    Check Out11 00

    Rated Average
    Midscale, smoke-free hotel near Washington College 3 floors, 81 rooms and suites - elevator
    Heated indoor swimming pool - exercise room
    Microwave and refrigerator in every room
    Free hot breakfast buffet
    Free Internet in room
    Free parking
    Pet-friendly hotel - allows pets up to 15 pounds - $50 per stay pet fee up to 7 nights. - Sep 2015

    Most Recent HotelGuides Review
    "My hotel stay was fair.2017-05-02"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 156 reviews  Read Recent Reviews

  • 11 miles Haven Point Inn
    20748 Rock Hall Avenue, Rock Hall, MD 21661
    11 miles from Chestertown
    From $135
    Enter Dates
    Haven Point Inn Rock Hall

    Check In14 00
    Check Out11 00

    Rated Very High
    Midscale, smoke-free inn near the beach and The Haven Short walk to beach
    2 floors, 4 rooms - no elevator
    No swimming pool
    Free continental breakfast
    Free Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Jun 2017

    TripAdvisor Traveler Rating:  5.0 of 5 stars
    Based on 17 reviews  Read Recent Reviews

  • 19 miles Holiday Inn Express
    1020 Kent Narrows Road, Grasonville, MD 21638
    19 miles from Chestertown
    From $112
    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
    3 floors, 76 rooms - elevator
    Outdoor swimming pool open in summer
    Free hot breakfast buffet
    Free Internet in room
    Free parking - truck parking
    Not pet-friendly - no pets allowed. - Jan 2016

    Most Recent HotelGuides Review
    "Good location - room had a beautiful view - had trouble with the key card.2009-08-01"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 223 reviews  Read Recent Reviews

  • 19 miles Best Western Kent Narrows Inn
    3101 Main Street, Grasonville, MD 21638
    19 miles from Chestertown
    From $99
    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
    4 floors, 72 rooms and suites - AAA 2 Diamonds
    Heated indoor swimming pool - exercise room
    Free hot breakfast buffet
    Free Internet in room
    Free parking - truck parking
    Not pet-friendly - no pets allowed. - Mar 2016

    Most Recent HotelGuides Review
    "I wasn't informed that the motel was undergoing renovations. 2016-03-01"
    More >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 446 reviews  Read Recent Reviews

  • 19 miles Hilton Garden Inn Kent Island
    3206 Main Street, Grasonville, MD 21638
    19 miles from Chestertown
    From $303
    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
    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 Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Sep 2015

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 830 reviews  Read Recent Reviews

  • 20 miles Home2 Suites
    20 Newton Road, Aberdeen, MD 21001
    20 miles from Chestertown
    From $152
    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
    5 floors, 107 studio and one-bedroom suites
    Indoor swimming pool - exercise rooom
    Kitchen in every suite
    Free continental breakfast
    Free Internet in room
    Free parking
    Pet-friendly hotel - allows pets up to 75 pounds - $75 per stay fee for each pet. - Sep 2015

    Most Recent HotelGuides Review
    "Good hotel, but my room smelled like cheap cologne, and the linens were dirty. There was food from the previous guest in the fridge. To say I was shocked would be an understatement.2015-11-25"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 272 reviews  Read Recent Reviews

  • 21 miles Holiday Inn
    1326 Policy Drive, Belcamp, MD 21017
    21 miles from Chestertown
    From $109
    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
    3 floors, 107 rooms - elevator
    Heated indoor swimming pool - exercise room
    Microwave and refrigerator in every room
    Free hot breakfast buffet
    Free Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Sep 2015

    Most Recent HotelGuides Review
    "Convenient to Havre De Grace. Nice hotel room. There was a Burger King next door.2016-06-11"
    More >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 652 reviews  Read Recent Reviews

  • 21 miles Sleep Inn
    1807 Edgewood Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $63
    Enter Dates
    Sleep Inn Edgewood

    Check In15 00
    Check Out11 00

    Rated Average
    Midscale, smoke-free, interstate hotel
    Near I-95, Exit 77
    3 floors, 848 rooms and suites - elevator
    Heated indoor swimming pool - exercise room
    Microwave and refrigerator in every room
    Free continental breakfast
    Free Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Sep 2015

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 246 reviews  Read Recent Reviews

  • 21 miles Homewood Suites
    4170 Philadelphia Road, Bel Air, MD 21015
    21 miles from Chestertown
    From $104
    Enter Dates
    Homewood Suites by Hilton Bel Air

    Check In15 00
    Check Out12 00

    Rated Very High
    Upscale, 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 Internet in room
    Free parking - truck parking
    Pet-friendly hotel - allows pets up to 75 pounds, 1 pet per room - $75 per stay pet fee. - Jan 2016

    Most Recent HotelGuides Review
    "The hotel was clean and beautiful. I had a wonderful stay.2017-03-14"


    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 343 reviews  Read Recent Reviews

  • 21 miles Holiday Inn Express
    2118 Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $179
    Enter Dates
    Holiday Inn Express Edgewood

    Check In15 00
    Check Out11 00

    Rated High
    Midscale, smoke-free, interstate hotel near I-95, Exit 77 3 floors, 92 rooms and suites - elevator
    Heated indoor swimming pool - exercise room
    Microwave and refrigerator in every room
    Free hot breakfast buffet
    Free Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Sep 2015

    Most Recent HotelGuides Review
    "Our room was nice and clean, and everything was in good working order. The staff was friendly and helpful. I'd stay at this hotel again.2015-10-20"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 93 reviews  Read Recent Reviews

  • 21 miles Comfort Inn & Suites
    2112 A Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $85
    Enter Dates
    Comfort Inn & Suites Edgewood

    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 Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Sep 2015

    Most Recent HotelGuides Review
    "The hotel and room were clean, and a breakfast with hot selections was included. This was a good choice.2017-04-10"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 137 reviews  Read Recent Reviews

  • 21 miles Super 8 Motel
    1015 Pulaski Highway, Joppa, MD 21085
    21 miles from Chestertown
    From $68
    Enter Dates
    Super 8 Motel Joppa

    Check In1600
    Check Out1100

    Rated Average
    Cheap hotel 10 miles from Aberdeen Proving Ground This hotel is 20 miles northeast of downtown Baltimore.
    2 floors, 55 rooms - no elevator
    No swimming pool
    Free continental breakfast
    Free Internet in room
    Free parking - truck parking
    Pet-friendly hotel - allows up to 3 pets per room - $10 per night fee for each pet. - Nov 2016

    Most Recent HotelGuides Review
    "The room was nice, and the grounds were wonderful for walking my dog. I highly recommend this hotel.2017-04-11"
    More >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 168 reviews  Read Recent Reviews

  • 21 miles Candlewood Suites
    4216 Philadelphia Road, Bel Air, MD 21015
    21 miles from Chestertown
    From $120
    Enter Dates
    Candlewood Suites Bel Air

    Check In15 00
    Check Out12 00

    Rated High
    Midscale, all-suite, extended-stay hotel 6 miles West of Aberdeen Proving Ground
    3 floors, 95 suites - elevator
    No swimming pool
    Exercise room
    Kitchen in every suite
    Free Internet in room
    Free parking
    Pet-friendly hotel - allows pets up to 80 pounds, 2 pets per room - $15 pet fee for 1st night - $10 fee for each night thereafter - $150 maximum per stay pet fee. - Sep 2016

    Most Recent HotelGuides Review
    "Clean and pet-friendly. Staff was congenial. We stay here every year, and it's always very nice.2015-01-18"


    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 116 reviews  Read Recent Reviews

  • 21 miles Red Roof Inn
    2116 Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $65
    Enter Dates
    Red Roof Inn Edgewood

    Check In14 00
    Check Out11 00

    Rated Average
    Cheap, interstate motel near I-95, Exit 77 2 floors, 72 rooms - no elevator
    No swimming pool
    Microwave and refrigerator in every room
    Free continental breakfast
    Free Internet in room
    Free parking
    Pet-friendly motel - allows 1 pet per room - no pet fee. - May 2016

    Most Recent HotelGuides Review
    "Good rates - I was satisfied.2011-07-01"
    More >

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 131 reviews  Read Recent Reviews

  • 21 miles Extended Stay America Hotel
    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 3 floors, 101 suites - elevator
    No swimming pool
    Kitchen in every suite
    Free continental breakfast
    Free Internet in room
    Free parking
    Pet-friendly hotel - $25 per night fee for each pet - $150 maximum per stay fee for each pet. - Sep 2015

    Most Recent HotelGuides Review
    "Room wasn't clean enough; carpet hadn't been vacuumed, and we found garbage in the kitchenette - bathroom smelled like smoke - a disgusting stay.2008-08-01"


    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 36 reviews  Read Recent Reviews

  • 21 miles Ramada Hotel & Conference Center
    1700 Van Bibber Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $77
    Enter Dates
    Ramada Hotel & Conference Center Edgewood

    Check In1500
    Check Out1100

    Rated Average
    Midscale, interstate motel near I-95, Exit 77 2 floors, 152 rooms - no elevator
    Outdoor swimming pool open in summer - exercise room
    Microwave and refrigerator in every room
    Free continental breakfast
    Free Internet in room
    Free parking
    Pet-friendly motel - $25 per night fee for each pet. - Sep 2015

    Most Recent HotelGuides Review
    "Housekeeping didn't leave fresh towels or washcloths for 2 days - someone tried to enter our room despite the "Do Not Disturb" sign on the door - easy check-in.2010-11-01"
    More >

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 323 reviews  Read Recent Reviews

  • 21 miles La Quinta Inn & Suites
    2112-B Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $109
    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
    3 floors, 64 rooms and suites - elevator
    No swimming pool
    Exercise room
    Microwave and refrigerator in every room
    Free continental breakfast
    Free Internet in room
    Free parking
    Pet-friendly hotel - allows up to 2 pets per room - no pet fee. - Sep 2015

    Most Recent HotelGuides Review
    "The hotel was pet-friendly, and the employees were extremely nice. We forgot something in the room, and the housekeeper came to our car to give it to us. I highly recommend staying here.2017-09-19"
    More >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 332 reviews  Read Recent Reviews

  • 21 miles SpringHill Suites
    1420 Handlir Drive, Bel Air, MD 21015
    21 miles from Chestertown
    From $189
    Enter Dates
    SpringHill Suites by Marriott Bel Air

    Check In1500
    Check Out1200

    Rated High
    Midscale, 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 Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Sep 2015

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 164 reviews  Read Recent Reviews

  • 21 miles Country Inn & Suites by Carlson
    1435 Handlir Drive, Bel Air, MD 21015
    21 miles from Chestertown
    From $106
    Enter Dates
    Country Inn & Suites by Carlson Bel Air

    Check In15 00
    Check Out12 00

    Rated High
    Midscale 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 Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Sep 2015

    Most Recent HotelGuides Review
    "Not such a great hotel room, and the bathroom was one of the worst I've come across in recent years. The employees were nice, but I wouldn't stay here again.2016-10-16"
    More >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 502 reviews  Read Recent Reviews

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Chestertown Info

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Map of Chestertown MD Hotels


Hotels near
Nearby Attractions


Hotels near Washington College
   0.4 mile north
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 Aspen Wye River Conference Center
   21 miles south
Hotels near Perry Point VA Medical Center
   23 miles north
Hotels near Johns Hopkins Bayview Medical Center
   26 miles west
Hotels near Anne Arundel Community College
   26 miles SW
Hotels near APG Federal Credit Union Arena
   26 miles NW
Hotels near Harford Community College
   27 miles NW
Hotels near Alumni Hall
   27 miles SW
Hotels near US Naval Academy
   28 miles SW
Hotels near Fort McHenry National Monument
   28 miles west
Hotels near Navy Memorial Stadium
   28 miles SW
Hotels near Johns Hopkins Hospital
   28 miles west

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Rock Hall MD Hotels
   10 miles SW
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
Edgemere MD Hotels
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Abingdon MD Hotels
   21 miles NW
Stevensville MD Hotels
   21 miles SW
Aberdeen MD Hotels
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Middle River MD Hotels
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Essex MD Hotels
   23 miles west
Havre de Grace MD Hotels
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Chestertown Hotels, Motels, Lodging, and Accommodations – Chestertown, Maryland MD, USA



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