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How to get fromMassachusetts to Winchesterby plane, bus, train, bus (Flixbus), taxi, bus (Greyhound), or car

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There are 13 ways to get from Massachusetts to Winchester by plane, bus, train, bus (Flixbus), taxi, bus (Greyhound), or car

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 Boston Logan Airport 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
    5h 29m
    $560–1,175

  2. Drive 485.3 mi

    cheapest
    1. Drive from Boston to Winchestercar car 485.3 mi
    9h 6m
    $89–128

  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
    9h 48m
    $120–808

  4. Bus

    1. Take the bus from Boston to NYC Downtownbus bus FlixBus 2611
    2. Take the bus from New York to Winchesterbus bus Nyc
    10h 19m
    $96–145

  5. 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
    10h 35m
    $204–375

  6. Fly Bradley International Airport to Washington Dulles International Airport, bus

    1. Fly from Bradley International Airport (BDL) to Washington Dulles International Airport (IAD)plane plane BDL - IAD
    2. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    5h 35m
    $114–406

  7. Fly Boston Logan Airport 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
    6h 30m
    $546–1,467

  8. Fly Bradley International Airport to Ronald Reagan Washington National Airport, bus

    1. Fly from Bradley International Airport (BDL) to Ronald Reagan Washington National Airport (DCA)plane plane BDL - DCA
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    6h 31m
    $135–558

  9. Train to Theodore Francis Green State Airport, fly to Washington Dulles International Airport, bus

    1. Take the train from South Station to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Washington Dulles International Airport (IAD)plane plane PVD - IAD
    3. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    6h 34m
    $398–739

  10. Bus to Manchester Airport, fly to Washington Dulles International Airport, bus

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Washington Dulles International Airport (IAD)plane plane MHT - IAD
    3. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    6h 18m
    $131–477

  11. Fly Bradley International Airport to Baltimore-Washington International Airport, train, taxi

    1. Fly from Bradley International Airport (BDL) to Baltimore-Washington International Airport (BWI)plane plane BDL - 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
    7h 30m
    $125–1,023

  12. 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
    10h 36m
    $98–155

  13. Train, taxi

    1. Take the train from Boston to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station 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
    10h 37m
    $186–952

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

Calendar47Weekly Planes
Duration2h 38mAverage Duration
Ticket$57Cheapest Price
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Questions & Answers

Map of how to get from Massachusetts to Winchester.ExpandLaunch map view
  • Distance: 488.1 mi
  • Duration: 5h 29m

What companies run services between Massachusetts, USA and Winchester, VA, USA?

You can take a bus from Boston to Winchester via NYC Downtown, New York, and Winchester in around 10h 19m.

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