test Hotels & Motels near Chester, MD | HotelGuides.com
Our Customers Have Booked Over 5,000,000 Hotel Reservations
     
See Rates for Hotels near Chester
 Pet Friendly Only
 

HotelGuides.com > Maryland > Chester Hotels & Motels

Hotels and Motels near Chester, MD


Hotels below are sorted by distance from Chester.

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
 

Rates shown below are averages. Click See Rates to view rates for your dates.
  • 1.9 miles Inn at Chesapeake Bay Stevensville

    180 Pier One Road, Stevensville, MD 21666
    1.9 miles from Chester

    Enter 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
    • No swimming pool
    • Exercise room
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - Apr 2016
    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 145 reviews  Read Recent Reviews

  • 2.6 miles Best Western Kent Narrows Inn Grasonville

    3101 Main Street, Grasonville, MD 21638
    2.6 miles from Chester

    Enter Dates
    Best Western Kent Narrows Inn Grasonville

    Check In1600
    Check Out1100

    Rated High
    • 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 738 reviews  Read Recent Reviews

  • 2.7 miles Hilton Garden Inn Kent Island Grasonville

    3206 Main Street, Grasonville, MD 21638
    2.7 miles from Chester

    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
    • Heated indoor swimming pool - exercise 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 1039 reviews  Read Recent Reviews

  • 2.8 miles Holiday Inn Express Grasonville

    1020 Kent Narrows Road, Grasonville, MD 21638
    2.8 miles from Chester

    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
    • 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 256 reviews  Read Recent Reviews

  • 10 miles Rodeway Inn Annapolis

    74 Old Mill Bottom Road North, US 50, Exit 28, Annapolis, MD 21409
    10 miles from Chester

    Enter Dates
    Rodeway Inn Annapolis

    Check In15 00
    Check Out11 00

    Rated Average
    • Cheap motel 4 miles from Sandy Point State Park
    • Some smoking rooms
    • No swimming pool
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - Jul 2015

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 139 reviews  Read Recent Reviews

  • 11 miles Annapolis Waterfront Hotel

    80 Compromise Street, Annapolis, MD 21401
    11 miles from Chester

    Enter Dates
    Annapolis Waterfront Hotel

    Check In1600
    Check Out1100

    Rated High
    • Upper-upscale, smoke-free, full-service, waterfront hotel
    • Located in downtown Annapolis
    • An Autograph Collection hotel
    • No swimming pool
    • Exercise room
    • Free WiFi
    • Valet parking only - $30 per night
    Pet friendly hotel More >
    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 611 reviews  Read Recent Reviews

  • 11 miles Quality Inn US Naval Academy Annapolis

    76 Old Mill Bottom Road North, Annapolis, MD 21401
    11 miles from Chester

    Enter Dates
    Quality Inn US Naval Academy Annapolis

    Check In15 00
    Check Out11 00

    Rated High
    • Midscale, smoke-free hotel
    • 5.5 miles from near Sandy Point State Park
    • No swimming pool
    • Exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - Aug 2019

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 134 reviews  Read Recent Reviews

  • 11 miles Historic Inns Annapolis

    58 State Circle, Annapolis, MD 21401
    11 miles from Chester

    Enter 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
    • Free shuttle to local attractions
    • No swimming pool
    • Exercise room
    • Free WiFi
    • Valet parking only - $30 per night
    Not pet friendly - no pets allowed. - Feb 2020

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 1434 reviews  Read Recent Reviews

  • 11 miles Graduate Hotel Annapolis

    126 West Street, Annapolis, MD 21401
    11 miles from Chester

    Enter Dates
    Graduate Hotel Annapolis

    Check In16 00
    Check Out11 00

    Rated High
    • Upper-upscale, smoke-free, downtown hotel
    • Near historic district
    • No swimming pool
    • 24-hour exercise room
    • Free WiFi
    • Parking costs $26 per night
    Pet friendly hotel More >

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 239 reviews  Read Recent Reviews

  • 11 miles Hilton Garden Inn Downtown Annapolis

    174 West Street, Annapolis, MD 21401
    11 miles from Chester

    Enter Dates
    Hilton Garden Inn Downtown Annapolis

    Check In15 00
    Check Out12 00

    Rated High
    • Upscale, smoke-free, downtown hotel
    • No swimming pool
    • Exercise room
    • Free WiFi
    • Valet parking only - $26 per night
    Not pet friendly - no pets allowed. - Jul 2018
    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 221 reviews  Read Recent Reviews

  • 13 miles Inn at Perry Cabin St Michaels

    308 Watkins Lane, St Michaels, MD 21663
    13 miles from Chester

    Enter 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
    • Outdoor swimming pool open in summer - exercise room
    • 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 1330 reviews  Read Recent Reviews

  • 13 miles Westin Hotel Annapolis

    100 Westgate Circle, Annapolis, MD 21401
    13 miles from Chester

    Enter Dates
    Westin Hotel Annapolis

    Check In1600
    Check Out1100

    Rated High
    • Upscale, smoke-free, full-service, downtown Annapolis hotel
    • Heated indoor swimming pool - exercise room
    • 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 1119 reviews  Read Recent Reviews

  • 13 miles Crowne Plaza Hotel Annapolis

    173 Jennifer Road, Annapolis, MD 21401
    13 miles from Chester

    Enter 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
    • Free WiFi
    • Free parking
    Pet friendly hotel More >

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 678 reviews  Read Recent Reviews

  • 14 miles Holiday Inn Express & Suites Annapolis

    2451 Riva Road, Annapolis, MD 21401
    14 miles from Chester

    Enter Dates
    Holiday Inn Express & Suites Annapolis

    Check In15 00
    Check Out11 00

    Rated High
    • Upper-midscale, smoke-free hotel
    • Near Annapolis Mall and US Navel Academy
    • No swimming pool
    • Exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - Jul 2021

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 410 reviews  Read Recent Reviews

  • 14 miles Extended Stay America Suites Annapolis

    1 Womack Drive, Annapolis, MD 21401
    14 miles from Chester

    Enter Dates
    Extended Stay America Suites Annapolis

    Check In15 00
    Check Out11 00

    Rated Average
    • Budget, all-suite, extended-stay hotel near Annapolis Mall
    • Some smoking rooms
    • No swimming pool
    • Kitchen in every suite
    • Free continental breakfast
    • Free WiFi
    • Free parking
    Pet friendly hotel More >

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 140 reviews  Read Recent Reviews

  • 14 miles DoubleTree by Hilton Hotel Annapolis

    210 Holiday Court, Annapolis, MD 21401
    14 miles from Chester

    Enter Dates
    DoubleTree by Hilton Hotel Annapolis

    Check In16 00
    Check Out12 00

    Rated High
    • Upscale, smoke-free, full-service hotel near Annapolis Mall
    • Free shuttle to attractions within 5-mile radius
    • Outdoor swimming pool open in summer - exercise room
    • Free WiFi
    • Free parking
    Pet friendly hotel More >

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 1432 reviews  Read Recent Reviews

  • 14 miles Best Western Annapolis Hotel

    2520 Riva Road, Building B, Annapolis, MD 21401
    14 miles from Chester

    Enter Dates
    Best Western Annapolis Hotel

    Check In1500
    Check Out1100

    Rated Average
    • Midscale motel near Annapolis Mall
    • Some smoking rooms
    • Outdoor swimming pool open in summer - exercise room
    • Free continental breakfast
    • Free WiFi
    • Free parking - truck parking
    Pet friendly motel More >

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 620 reviews  Read Recent Reviews

  • 14 miles Red Roof Inn West Annapolis

    2520 Riva Road, Building C, Annapolis, MD 21401
    14 miles from Chester

    Enter 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
    • No swimming pool
    • 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 17 reviews  Read Recent Reviews

  • 14 miles Hampton Inn & Suites Annapolis

    124 Womack Drive, Annapolis, MD 21401
    14 miles from Chester

    Enter Dates
    Hampton Inn & Suites Annapolis

    Check In15 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 >

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 1024 reviews  Read Recent Reviews

  • 14 miles SpringHill Suites by Marriott Annapolis

    189 Admiral Cochrane Drive, Annapolis, MD 21401
    14 miles from Chester

    Enter Dates
    SpringHill Suites by Marriott Annapolis

    Check In1500
    Check Out1200

    Rated Very High
    • Upscale, smoke-free, all-suite hotel
    • Located near Annapolis Mall
    • Heated indoor swimming pool - exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - Aug 2016

    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 719 reviews  Read Recent Reviews

  • Why Book Here?
    • We add no fees.
    • Lowest price guarantee
    • Pay at hotel in most cases
    • If you don't like your hotel,
      we'll refund your money.
    • Cash rewards + hotel points too
  • See more reasons
 
Chester Info

Chester Group Hotel Rates

Hotels near Me

Nearby Attractions


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 Sandy Point State Park   7 miles NW
Hotels near Queenstown Premium Outlets   7 miles east
Hotels near Naval Support Activity Annapolis   10 miles west
Hotels near Chesapeake Bay MD   10 miles SW
Hotels near Aspen Wye River Conference Center   10 miles SE
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 US Naval Academy Museum   11 miles west
Hotels near Annapolis Waterfront   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
Cape St Claire MD Hotels   10 miles NW
Annapolis MD Hotels   11 miles west
Rock Hall MD Hotels   11 miles north
Wye Mills MD Hotels   11 miles east
Arnold MD Hotels   12 miles west
Centreville MD Hotels   13 miles east
St Michaels MD Hotels   14 miles south
Lake Shore MD Hotels   14 miles NW
Londontown MD Hotels   15 miles west
Earn Cash Rewards plus Hotel Reward Points
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.
Hotel Tips

Important Hotel Tips


Chester Hotels near Me

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

© 2021 HotelGuides.com, Inc. All rights reserved.

About Us | Terms of Use | Privacy Policy | Security | Contact Us


Home - HotelGuides.com US Hotels Canada Hotels Hotels in other countries View, change, or cancel my reservations Customer Service Our Better Business Bureau rating is A+ Hotel Guides is Made in USA
Hotel Guides

Just a moment while

we find the best deals

at the best hotels.