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How to get fromBoston Airport (BOS) to Winchesterby plane, bus, train, rideshare, car, taxi, bus (Flixbus), or bus (Greyhound)

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There are 9 ways to get from Boston Airport (BOS) to Winchester by plane, bus, train, rideshare, car, taxi, bus (Flixbus), or bus (Greyhound)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly to Washington Dulles International Airport, bus

    best
    1. Fly from Boston Logan Airport (BOS) to Washington Dulles International Airport (IAD)plane plane BOS - IAD
    2. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    3h 59m
    $564–1,144

  2. Drive 488.4 mi

    cheapest
    1. Drive from Boston Airport (BOS) to Winchestercar car 488.4 mi
    9h 10m
    $90–129

  3. Train, bus via New York

    1. Take the train from Boston to Ny Moynihan Train Hall At Penn Stationtrain train Northeast Regional
    2. Take the bus from New York to Winchesterbus bus Nyc
    10h 38m
    $125–853

  4. Train, bus

    1. Take the train from Boston to Washington Union Stationtrain train Acela
    2. Take the bus from Washington Union Station to Front Royal Walmartbus bus Valley Flyer
    11h 35m
    $210–386

  5. Airport Transfer

    1. Take the rideshare from Boston-BOS to Winchesterrideshare rideshare 488.4 mi
    9h 10m

  6. Fly to Ronald Reagan Washington National Airport, bus

    1. Fly from Boston Logan Airport (BOS) to Ronald Reagan Washington National Airport (DCA)plane plane BOS - DCA
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    5h 1m
    $546–1,242

  7. Fly to Baltimore-Washington International Airport, train, taxi

    1. Fly from Boston Logan Airport (BOS) to Baltimore-Washington International Airport (BWI)plane plane BOS - BWI
    2. Take the train from BWI Thurgood Marshall to Washington Union Stationtrain train
    3. Take the train from Washington Union Station to DUFFIELDS W VA MARC wbtrain train
    4. Take the taxi from DUFFIELDS W VA MARC wb to Winchestertaxi taxi
    5h 46m
    $206–1,595

  8. Bus

    1. Take the bus from Boston to NYC Downtownbus bus FlixBus 2611
    2. Take the bus from New York to Winchesterbus bus Nyc
    11h 44m
    $102–157

  9. Bus via New York

    1. Take the bus from Boston to Port Authority Bus Terminalbus bus Greyhound US0230 / ...
    2. Take the bus from New York to Winchesterbus bus Nyc
    11h 58m
    $105–170

Boston Logan Airport (BOS) to Washington Dulles International Airport (IAD) flights

Calendar47Weekly Planes
Duration2h 38mAverage Duration
Ticket$58Cheapest Price
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Questions & Answers

Map of how to get from Boston Airport (BOS) to Winchester.ExpandLaunch map view
  • Distance: 485 mi
  • Duration: 3h 59m

What companies run services between Boston Airport (BOS), USA and Winchester, VA, USA?

You can take a bus from Logan International Airport to Winchester via Boston, South Station, Boston, NYC Downtown, New York, and Winchester in around 11h 44m.

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