Chestertown, MD Limo Service
Chestertown is the Kent County seat and one of the Eastern Shore's best-preserved colonial towns, a waterfront community on the Chester River built around Washington College and a historic downtown of brick row houses and working wharves. BWI Chauffeur serves Chestertown's historic district, the Washington College campus and the surrounding farm country with flat-rate sedans, SUVs and Sprinter vans for airport transfers, weddings and college travel.
The trip across the Bay Bridge adds real distance — BWI is 55 miles away, typically 70 to 85 minutes via US-301 and the Bay Bridge, while Reagan National (75 miles) and Dulles (90 miles) are both longer hauls through the same corridor. We quote every Chestertown trip as a single flat rate that accounts for the bridge crossing, not a per-mile surprise.
55 mi · 70–85 minutes
75 mi · 95–110 minutes
90 mi · 110–130 minutes
24 / 7
Reserve your chauffeur
Flat rate. Flight tracked. Real chauffeur.
Why choose BWI Chauffeur for Chestertown
Flat rate to BWI, DCA or Dulles — quoted before you book, including the Bay Bridge crossing
Door-to-door pickups across downtown Chestertown, the Washington College campus and surrounding Kent County
Real-time flight tracking with 45 minutes of free wait time on domestic arrivals and 60 on international
Chauffeurs who know Bay Bridge traffic patterns and the US-301/US-50 split, not just the map distance
Sprinter vans and a stretch limousine for Chester River weddings, graduations and family-weekend travel
Maryland PSC Carrier No. 6325 — fully licensed, commercially insured, background-checked chauffeurs
Serving Chestertown and the Chester River
Our coverage includes Chestertown's historic downtown, the Washington College campus, and the farm country and waterfront communities surrounding the Chester River. A chauffeur stages ahead of your pickup time, so a dawn departure from a Kent County farmhouse gets the same reliability as a campus pickup outside a Washington College dormitory.
The Bay Bridge crossing, built into the rate
Reaching any major airport from Chestertown means crossing the Chesapeake Bay Bridge, and that crossing is already built into your quoted flat rate — no surprise toll add-on at drop-off. BWI is roughly 70 to 85 minutes via US-301 and US-50, and we flight-track every airport leg so a delayed arrival never threatens your return trip home.
Washington College travel and Eastern Shore weddings
Families moving students in and out for Washington College's semester and graduation schedule rely on us for reliable airport-to-campus transfers, and the town's waterfront venues and farm estates host a steady calendar of weddings throughout the warmer months. A 14-passenger Sprinter keeps a wedding party or visiting family together for the whole weekend.
A historic downtown built for walking, not driving
Chestertown's downtown of 18th- and 19th-century brick row houses along High Street and the Chester River wharves is best experienced on foot once you arrive, which is exactly why we drop guests directly at a hotel, inn or waterfront restaurant rather than leaving them to find parking in a historic district with limited spaces. Visitors attending the town's seasonal festivals, the Chestertown Tea Party reenactment or a Washington College event appreciate not having to think about where the car goes for the rest of the day.
Vehicles available for Chestertown
Business sedan
Mercedes-Benz E-Class
Up to 3 passengers · solo executives and couples
First-class sedan
BMW 7 Series
Up to 3 passengers · VIP and executive travel
Premium SUV
Cadillac Escalade
Up to 6 passengers · families and small groups with luggage
Luxury SUV
Chevrolet Suburban
Up to 6 passengers · airport runs with extra luggage or gear
Executive van
Mercedes Sprinter van
Up to 14 passengers · wedding parties, corporate teams and groups
Limousine
Stretch limousine
Up to 8 passengers · proms, weddings and celebrations
Licensed & Insured
Maryland PSC Carrier No. 6325
BWI · DCA · IAD
45–60 min free wait
24 / 7 Dispatch
Same-day bookings welcome
Ready to book Chestertown?
One locked-in flat rate — call 877-609-1919 or request a quote online. No surge, no surprise. A real chauffeur, a real vehicle and a guaranteed pickup.
Booking Chauffeured Car Service in Chestertown, MD
Request a quote online or call 877-609-1919 with your pickup address, date and passenger count. Airport transfers to BWI, DCA and IAD are flat-rate; hourly chauffeur service covers multi-stop days and evenings out.
BWI Chauffeur confirms the rate before you ride, tracks every inbound flight, and keeps dispatch staffed 24/7 so a change of plans in Chestertown, MD is a phone call, not a problem.
Frequently asked questions
How much is a car service from BWI to Chestertown, MD?
It is a single flat rate based on your pickup and drop-off address, confirmed before you book, and it already includes the Bay Bridge toll. Call 877-609-1919 for the exact figure.
How long is the drive from Chestertown to BWI Airport?
Typically 70 to 85 minutes via US-301, the Bay Bridge and US-50, depending on bridge traffic — about 55 miles.
Do you serve Washington College for student move-in and graduation?
Yes. We regularly handle airport-to-campus transfers for Washington College families during move-in weekends and graduation.
Is the Bay Bridge toll included in the quoted rate?
Yes. The Bay Bridge toll is included in your flat rate, along with gratuity, so there is no additional charge added at drop-off.
Can you handle a wedding on the Chester River waterfront?
Yes. We regularly coordinate Chestertown-area wedding transportation, including Sprinter vans for the wedding party and sedans for out-of-town guests.