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Chestertown, MD Hotels & Motels | HotelGuides.com
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Hotels > US Hotels > Hotels in Maryland > Chestertown Hotels & Motels

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
 
  • Red Roof Inn & Suites Chestertown
    160 Scheeler Road, Chestertown, MD 21620 Call Us

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    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 >
  • TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 143 reviews 
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  • Comfort Inn & Suites Chestertown
    150 Scheeler Road, Chestertown, MD 21620 Call Us

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    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 >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 191 reviews 
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  • Holiday Inn Express Grasonville
    1020 Kent Narrows Road, Grasonville, MD 21638 Call Us 19 miles
    19 miles from Chestertown

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    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
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 266 reviews 
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  • Best Western Kent Narrows Inn Grasonville
    3101 Main Street, Grasonville, MD 21638 Call Us 19 miles
    19 miles from Chestertown

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    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 >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 818 reviews 
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  • Hyatt Place Hotel Kent Narrows & Marina Grasonville
    3028 Kent Narrow Way South, Grasonville, MD 21638 Call Us 19 miles
    19 miles from Chestertown

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    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 >

  • Hilton Garden Inn Kent Island Grasonville
    3206 Main Street, Grasonville, MD 21638 Call Us 19 miles
    19 miles from Chestertown

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    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
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 1070 reviews 
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  • Home2 Suites by Hilton Aberdeen
    20 Newton Road, Aberdeen, MD 21001 Call Us 20 miles
    20 miles from Chestertown

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    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 >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 389 reviews 
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  • SpringHill Suites by Marriott Middle River
    6110 Greenleigh Avenue, Middle River, MD 21220 Call Us 20 miles
    20 miles from Chestertown

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    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
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 49 reviews 
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  • Holiday Inn Belcamp - I-95, Exit 80
    1326 Policy Drive, I-95, Exit 80, Belcamp, MD 21017 Call Us 21 miles
    21 miles from Chestertown

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    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
  • TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 30 reviews 
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  • Ramada Hotel & Conference Center Edgewood - I-95, Exit 77
    1700 Van Bibber Road, I-95, Exit 77, Edgewood, MD 21040 Call Us 21 miles
    21 miles from Chestertown

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    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 - truck parking
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 362 reviews 
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  • Quality Inn & Suites Edgewood - I-95, Exit 77
    2112-A Emmorton Park Road, I-95, Exit 77, Edgewood, MD 21040 Call Us 21 miles
    21 miles from Chestertown

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    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
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 198 reviews 
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  • Holiday Inn Express Edgewood - I-95, Exit 77
    2118 Emmorton Park Road, I-95, Exit 77, Edgewood, MD 21040 Call Us 21 miles
    21 miles from Chestertown

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    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
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 118 reviews 
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  • TownePlace Suites by Marriott Belcamp - I-95, Exit 80
    1357 Belcamp Road, I-95, Exit 80, Belcamp, MD 21017 Call Us 21 miles
    21 miles from Chestertown

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    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 >

  • Red Roof Inn Edgewood - I-95, Exit 77
    2116 Emmorton Park Road, I-95, Exit 77, Edgewood, MD 21040 Call Us 21 miles
    21 miles from Chestertown

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    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 
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  • Extended Stay America Suites Bel Air - I-95, Exit 80
    1361 James Way, I-95, Exit 80, Bel Air, MD 21015 Call Us 21 miles
    21 miles from Chestertown

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

    Check In15 00
    Check Out11 00

    Rated Average
    • 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 
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  • Country Inn & Suites by Radisson Bel Air - I-95, Exit 80
    1435 Handlir Drive, I-95, Exit 80, Bel Air, MD 21015 Call Us 21 miles
    21 miles from Chestertown

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    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
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 680 reviews 
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  • La Quinta Inn & Suites Edgewood - I-95, Exit 77
    2112-B Emmorton Park Road, I-95, Exit 77, Edgewood, MD 21040 Call Us 21 miles
    21 miles from Chestertown

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

    Check In15 00
    Check Out11 00

    Rated Average
    • 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 >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 482 reviews 
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  • Hilton Garden Inn Bel Air - I-95, Exit 80
    4160 Philadelphia Road, I-95, Exit 80, Bel Air, MD 21015 Call Us 21 miles
    21 miles from Chestertown

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    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 >

  • Homewood Suites by Hilton Bel Air - I-95, Exit 80
    4170 Philadelphia Road, I-95, Exit 80, Bel Air, MD 21015 Call Us 21 miles
    21 miles from Chestertown

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    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 >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 465 reviews 
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    More Reviews

  • SpringHill Suites by Marriott Bel Air - I-95, Exit 80
    1420 Handlir Drive, I-95, Exit 80, Bel Air, MD 21015 Call Us 21 miles
    21 miles from Chestertown

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    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
  • 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 Bengies Drive-In   20 miles NW
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 Kent Island Resort   22 miles SW
Hotels near Bay Bridge MD   22 miles SW
Hotels near Sandy Point State Park   22 miles SW

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
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.
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Hotel Booking Tips
  1. Beware of non-refundable reservations that could cost you a lot of money if you change or cancel them. +Non-refundable reservations are a gamble that will usually save you less than $10. If you make a $90 non-refundable reservation instead of a $100 refundable booking, you are betting $90 to win $10. Would you do that in Las Vegas?
  2. Don't assume you can cancel a non-refundable reservation without penalty if you notify the hotel weeks or even months in advance. +Often you cannot – because some hotels' profit strategy is to get paid more than once for the same room for the same night.
  3. Always read cancellation policies carefully before you make a reservation. + When is the latest date and time you can cancel without penalty?
    More >
  4. When you make a reservation, you will receive a confirmation email. Take a copy with you to the hotel.
  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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