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Hotel Guides > Maryland > Chestertown Hotels & Motels

Hotels in or near Chestertown, Maryland

Hotel DescriptionsMap of Hotels

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

Zoom in (+) to see interstate exits, restaurants, and other attractions near 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 $99
    Enter Dates
    Quality Suites Chestertown

    Check In15 00
    Check Out11 00

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

    Most Recent HotelGuides Review
    "We enjoyed our hotel stay. The room was spacious and pretty quiet, and the amenities were nice. The only drawback was that the pillows weren't comfortable. The front desk clerk was friendly. Good continental breakfast. We were able to keep our bikes in our room, and it was a short walk to an excellent restaurant for dinner. Don't hesitate to stay here.2018-06-03"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 124 reviews  Read Recent Reviews

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

    From $259
    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 WiFi
    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"


    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 167 reviews  Read Recent Reviews

  • 11 miles Haven Point Inn Rock Hall
    20748 Rock Hall Avenue, Rock Hall, MD 21661
    11 miles from Chestertown
    From $155
    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 WiFi
    Free parking
    Not pet friendly - no pets allowed. - Jun 2017

    TripAdvisor Traveler Rating:  5.0 of 5 stars
    Based on 24 reviews  Read Recent Reviews

  • 19 miles Sleep Inn Grasonville
    101 VFW Avenue, Grasonville, MD 21638
    19 miles from Chestertown
    From $180
    Enter Dates
    Sleep Inn Grasonville

    Check In15 00
    Check Out11 00

    Rated Average
    Midscale, smoke-free hotel 2 miles southeast of Kent Narrows
    2 floors, 59 rooms - no elevator
    Outdoor swimming pool open in summer
    Free continental breakfast
    Free WiFi - truck parking
    Free parking
    Not pet friendly - no pets allowed. - Sep 2015

    Most Recent HotelGuides Review
    "Great value. The hotel clerk was extremely friendly and helpful.2017-03-06"
    More >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 153 reviews  Read Recent Reviews

  • 19 miles Holiday Inn Express Grasonville
    1020 Kent Narrows Road, Grasonville, MD 21638
    19 miles from Chestertown
    From $252
    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 WiFi
    Free parking - truck parking
    Not pet friendly - no pets allowed. - Jan 2016

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 235 reviews  Read Recent Reviews

  • 19 miles Best Western Kent Narrows Inn Grasonville
    3101 Main Street, Grasonville, MD 21638
    19 miles from Chestertown
    From $113
    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 WiFi
    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 531 reviews  Read Recent Reviews

  • 19 miles Hilton Garden Inn Kent Island Grasonville
    3206 Main Street, Grasonville, MD 21638
    19 miles from Chestertown
    From $304
    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 WiFi
    Free parking
    Not pet friendly - no pets allowed. - Sep 2015

    Most Recent HotelGuides Review
    "Everything about this hotel was fantastic, and there were great restaurants in the area. Ask for a room facing the water.2018-06-03"


    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 904 reviews  Read Recent Reviews

  • 20 miles Home2 Suites by Hilton Aberdeen
    20 Newton Road, Aberdeen, MD 21001
    20 miles from Chestertown
    From $142
    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 WiFi
    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 312 reviews  Read Recent Reviews

  • 20 miles SpringHill Suites by Marriott Middle River
    6110 Greenleigh Avenue, Middle River, MD 21220
    20 miles from Chestertown
    From $110
    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
    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 Review
    "I had a wonderful stay. The hotel was clean, and the food was good. Everything was just right.2018-07-19"


    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 13 reviews  Read Recent Reviews

  • 21 miles Holiday Inn Belcamp
    1326 Policy Drive, Belcamp, MD 21017
    21 miles from Chestertown
    From $120
    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
    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 Review
    "Convenient to Havre De Grace. Nice hotel room. There was a Burger King next door.2016-06-11"


    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 10 reviews  Read Recent Reviews

  • 21 miles Sleep Inn Edgewood
    1807 Edgewood Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $86
    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 WiFi
    Free parking
    Not pet friendly - no pets allowed. - Sep 2015

    Most Recent HotelGuides Review
    "A cheap place to sleep. The hotel room was small, and an ice bucket was used as the bathroom garbage can. There was a gap around the room door. The pool hours weren't guest-friendly.2018-04-22"


    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 280 reviews  Read Recent Reviews

  • 21 miles Homewood Suites by Hilton Bel Air
    4170 Philadelphia Road, Bel Air, MD 21015
    21 miles from Chestertown
    From $156
    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 WiFi
    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 378 reviews  Read Recent Reviews

  • 21 miles Holiday Inn Express Edgewood
    2118 Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $124
    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 WiFi
    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"


    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 101 reviews  Read Recent Reviews

  • 21 miles Comfort Inn & Suites Edgewood
    2112 A Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $80
    Enter Dates
    Comfort Inn & Suites Edgewood

    Check In15 00
    Check Out11 00

    Rated Average
    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. - Sep 2015

    Most Recent HotelGuides Review
    "The AC was broken, and there were filthy spots on the floor. Stay at another hotel.2018-05-01"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 157 reviews  Read Recent Reviews

  • 21 miles Super 8 Motel Joppa
    1015 Pulaski Highway, Joppa, MD 21085
    21 miles from Chestertown
    From $61
    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 WiFi
    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 184 reviews  Read Recent Reviews

  • 21 miles Candlewood Suites Bel Air
    4216 Philadelphia Road, Bel Air, MD 21015
    21 miles from Chestertown
    From $148
    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 WiFi
    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 124 reviews  Read Recent Reviews

  • 21 miles Red Roof Inn Edgewood
    2116 Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $61
    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 WiFi
    Free parking
    Pet friendly motel - allows 1 pet per room - no pet fee. - May 2016

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 140 reviews  Read Recent Reviews

  • 21 miles Extended Stay America Hotel Bel Air
    1361 James Way, Bel Air, MD 21015
    21 miles from Chestertown
    From $72
    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 WiFi
    Free parking
    Pet friendly hotel - $25 per night fee for each pet - $150 maximum per stay fee for each pet. - Sep 2015

    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 $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 WiFi
    Free parking
    Pet friendly motel - $25 per night fee for each pet. - Sep 2015

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 339 reviews  Read Recent Reviews

  • 21 miles La Quinta Inn & Suites Edgewood
    2112-B Emmorton Park Road, Edgewood, MD 21040
    21 miles from Chestertown
    From $84
    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 WiFi
    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 395 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 Queenstown Premium Outlets
   17 miles south
Hotels near Chesapeake College
   18 miles south
Hotels near Aberdeen Proving Ground
   19 miles north
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 White Marsh Mall
   24 miles NW
Hotels near Johns Hopkins Bayview Medical Center
   26 miles west
Hotels near East Baltimore
   26 miles west
Hotels near USNA – Naval Academy
   27 miles SW
Hotels near Pulaski Highway Baltimore
   27 miles west
Hotels near Navy Memorial Stadium
   28 miles SW
Hotels near Military Bowl
   28 miles SW
Hotels near Fells Point
   28 miles west
Earn Cash Rewards plus Hotel Reward Points

Nearby Cities


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
   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
Havre de Grace MD Hotels
   23 miles north

How Do We Order Hotels Below?

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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