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

Hotels and Motels near Chester, MD


Chester is on Kent Island in eastern Maryland. It is 44 miles southeast of Baltimore.


Note:  Add 20 miles for hotels in St Michaels.

Map of Hotels and Motels near Chester, MD
 

  • Inn at Chesapeake Bay Stevensville
    180 Pier One Road, Stevensville, MD 21666 Call Us 1.9 miles
    1.9 miles from Chester

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    Dates
    Inn at Chesapeake Bay Stevensville

    Check In16 00
    Check Out11 00

    Rated Very High
    • Upscale, smoke-free, full-service hotel
    • Near US 50 and Terrapin Beach Park
    • 3 floors, 44 rooms and suites - elevator
    • No swimming pool
    • Exercise room
    • 2 restaurants - lounge
    • Free WiFi
    • Free parking
    • Not pet friendly
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 179 reviews 
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  • Hyatt Place Hotel Kent Narrows & Marina Grasonville
    3028 Kent Narrow Way South, Grasonville, MD 21638 Call Us 2.5 miles
    2.5 miles from Chester

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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 >

  • Best Western Kent Narrows Inn Grasonville
    3101 Main Street, Grasonville, MD 21638 Call Us 2.6 miles
    2.6 miles from Chester

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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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  • Hilton Garden Inn Kent Island Grasonville
    3206 Main Street, Grasonville, MD 21638 Call Us 2.7 miles
    2.7 miles from Chester

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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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  • Holiday Inn Express Grasonville
    1020 Kent Narrows Road, Grasonville, MD 21638 Call Us 2.8 miles
    2.8 miles from Chester

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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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  • Annapolis Waterfront Hotel
    80 Compromise Street, Annapolis, MD 21401 Call Us 11 miles
    11 miles from Chester

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    Dates
    Annapolis Waterfront Hotel

    Check In1600
    Check Out1100

    Rated Average
    • Upper-upscale, smoke-free, full-service, waterfront hotel
    • Located in downtown Annapolis
    • An Autograph Collection hotel
    • 6 floors, 150 rooms and suites
    • No swimming pool
    • Exercise room
    • Restaurant - lounge - room service
    • Free WiFi
    • Valet parking only - $30 per night
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 636 reviews 
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  • Historic Inns Annapolis
    58 State Circle, Annapolis, MD 21401 Call Us 11 miles
    11 miles from Chester

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    Dates
    Historic Inns Annapolis

    Check In16 00
    Check Out11 00

    Rated High
    • Midscale, smoke-free, downtown Annapolis hotel
    • Near US Naval Academy
    • Member of Historic Hotels of America
    • 3 buildings - 4 floors; 124 rooms, 9 suites
    • Free shuttle to local attractions
    • No swimming pool
    • Exercise room
    • Lounge
    • Free WiFi
    • Valet parking only - $30 per night
    • Not pet friendly
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 1524 reviews 
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  • Graduate Hotel Annapolis
    126 West Street, Annapolis, MD 21401 Call Us 11 miles
    11 miles from Chester

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    Dates
    Graduate Hotel Annapolis

    Check In16 00
    Check Out11 00

    Rated Very High
    • Upper-upscale, smoke-free, downtown hotel
    • Near historic district
    • No swimming pool
    • 24-hour exercise room
    • Restaurant - lounge
    • Restaurant open for lunch and dinner only
    • Free WiFi
    • Parking costs $26 per night
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 729 reviews 
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    More Reviews

  • Hilton Garden Inn Downtown Annapolis
    174 West Street, Annapolis, MD 21401 Call Us 11 miles
    11 miles from Chester

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    Dates
    Hilton Garden Inn Downtown Annapolis

    Check In15 00
    Check Out12 00

    Rated High
    • Upscale, smoke-free, downtown hotel
    • 5 floors, 120 rooms and suites
    • No swimming pool
    • Exercise room
    • Restaurant - lounge - room service
    • Restaurant open for breakfast and dinner only
    • Microwave and refrigerator in every room
    • Free WiFi
    • Valet parking only - $26 per night
    • Not pet friendly
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 247 reviews 
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  • Westin Hotel Annapolis
    100 Westgate Circle, Annapolis, MD 21401 Call Us 12 miles
    12 miles from Chester

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    Dates
    Westin Hotel Annapolis

    Check In1600
    Check Out1100

    Rated High
    • Upscale, smoke-free, full-service, downtown Annapolis hotel
    • 6 floors, 225 rooms and suites
    • Heated indoor swimming pool - exercise room
    • Restaurant - lounge - room service
    • Internet access costs $10 per night
    • Parking costs $20 per night
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 1300 reviews 
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  • Inn at Perry Cabin St Michaels
    308 Watkins Lane, St Michaels, MD 21663 Call Us 13 miles
    13 miles from Chester

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    Dates
    Inn at Perry Cabin St Michaels

    Check In16 00
    Check Out11 00

    Rated Very High
    • Luxury, smoke-free, full-service, waterfront hotel
    • Located one-half mile north of downtown St Michaels
    • 3 floors, 78 rooms - elevator
    • Outdoor swimming pool open in summer Exercise room
    • Restaurant - lounge
    • Full-service spa
    • Pet friendly hotel More >
  • Note: This hotel charges a resort fee of 10% - includes parking and WiFi.
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 1355 reviews 
    Read Recent Reviews

  • Crowne Plaza Hotel Annapolis
    173 Jennifer Road, Annapolis, MD 21401 Call Us 13 miles
    13 miles from Chester

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    Dates
    Crowne Plaza Hotel Annapolis

    Check In16 00
    Check Out11 00

    Rated Average
    • Upscale, smoke-free, full-service hotel near Annapolis Mall
    • Heated indoor swimming pool - fitness center
    • Restaurant - lounge - room service
    • Restaurant open for breakfast and dinner only
    • Free WiFi
    • Free parking
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 743 reviews 
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    More Reviews

  • Holiday Inn Express & Suites Annapolis
    2451 Riva Road, Annapolis, MD 21401 Call Us 13 miles
    13 miles from Chester

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    Dates
    Holiday Inn Express & Suites Annapolis

    Check In15 00
    Check Out11 00

    Rated Average
    • Upper-midscale, smoke-free hotel
    • Near Annapolis Mall and US Navel Academy
    • 2 floors, 79 rooms and suites - elevator
    • No 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 419 reviews 
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  • DoubleTree by Hilton Hotel Annapolis
    210 Holiday Court, Annapolis, MD 21401 Call Us 14 miles
    14 miles from Chester

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    Dates
    DoubleTree by Hilton Hotel Annapolis

    Check In16 00
    Check Out12 00

    Rated High
    • Upscale, smoke-free, full-service hotel near Annapolis Mall
    • 6 floors, 219 rooms and suites
    • Free shuttle to attractions within 5-mile radius
    • Outdoor swimming pool open in summer Exercise room
    • Restaurant - lounge - room service
    • Free WiFi
    • Free parking
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 1466 reviews 
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    More Reviews

  • Best Western Annapolis Hotel
    2520 Riva Road, Building B, Annapolis, MD 21401 Call Us 14 miles
    14 miles from Chester

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    Dates
    Best Western Annapolis Hotel

    Check In1500
    Check Out1100

    Rated Average
    • Midscale motel near Annapolis Mall
    • 2 floors, 151 rooms - no elevator
    • Some smoking rooms
    • Outdoor swimming pool open in summer Exercise room
    • Free continental breakfast
    • Free WiFi
    • Free parking - truck parking
    • Pet friendly motel More >
  • TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 639 reviews 
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    More Reviews

  • Red Roof Inn West Annapolis
    2520 Riva Road, Building C, Annapolis, MD 21401 Call Us 14 miles
    14 miles from Chester

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    Dates
    Red Roof Inn West Annapolis

    Check In15 00
    Check Out11 00

    Rated High
    • Cheap, smoke-free hotel near Ann Arundel Medical Center
    • Also near US 50 at MD 665
    • 2 floors, 47 rooms - no elevator
    • No swimming pool
    • Free WiFi
    • Free parking - truck parking
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 17 reviews 
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    More Reviews

  • Hampton Inn & Suites Annapolis
    124 Womack Drive, Annapolis, MD 21401 Call Us 14 miles
    14 miles from Chester

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    Dates
    Hampton Inn & Suites Annapolis

    Check In16 00
    Check Out11 00

    Rated High
    • Upper-midscale, smoke-free hotel near Annapolis Mall
    • Heated outdoor swimming pool open in summer
    • Exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 1041 reviews 
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    More Reviews

  • SpringHill Suites by Marriott Annapolis
    189 Admiral Cochrane Drive, Annapolis, MD 21401 Call Us 14 miles
    14 miles from Chester

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    Dates
    SpringHill Suites by Marriott Annapolis

    Check In1500
    Check Out1200

    Rated Very High
    • Upscale, smoke-free, all-suite hotel
    • Located near Annapolis Mall
    • 4 floors, 120 studio suites
    • 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:  4.5 of 5 stars
    Based on 729 reviews 
    Read Recent Reviews
    More Reviews

Great overall experience. I also want to highlight their $50 rewards program. Be sure to check that.

- Brandon Vaughn
  • Why Book Here?
    • Pay at hotel
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    • Lowest price
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  • See more reasons
Chester Info

Chester Group Hotel Rates

Hotels near Me

Nearby Attractions


Hotels near Kent Island Resort   1.6 miles SW
Hotels near Red Eye's Dock Bar   2.3 miles east
Hotels near Chesapeake Bay Beach Club   2.4 miles west
Hotels near Jetty Dock Bar   2.6 miles east
Hotels near Bay Bridge MD   4.3 miles west
Hotels near Kentmorr Restaurant   6 miles SW
Hotels near Sandy Point State Park   7 miles NW
Hotels near Annapolis Maritime Museum   10 miles west
Hotels near Chesapeake Bay MD   10 miles SW
Hotels near USNA – Naval Academy   10 miles west
Hotels near Annapolis Harbor   11 miles west
Hotels near Annapolis City Dock   11 miles west
Hotels near Annapolis Boat Show   11 miles west
Hotels near Annapolis Waterfront   11 miles west
Hotels near Maryland State House   11 miles west

Nearby Cities


Stevensville MD Hotels   1.4 miles west
Kent Narrows MD Hotels   2.8 miles east
Kent Island MD Hotels   3.4 miles SW
Grasonville MD Hotels   4.2 miles east
Queenstown MD Hotels   7 miles east
Chesapeake Bay MD Hotels   10 miles SW
Annapolis MD Hotels   11 miles west
Arnold MD Hotels   12 miles west
Centreville MD Hotels   13 miles east
St Michaels MD Hotels   14 miles south
Edgewater MD Hotels   15 miles west
Severna Park MD Hotels   15 miles NW
Crownsville MD Hotels   17 miles west
Pasadena MD Hotels   18 miles NW
Georgetown MD Hotels   18 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.
Book Group Reservations
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.



Hotels, Motels, Lodging, and Accommodations near Chester - Chester, Maryland MD, USA

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